Retrosynthesis route analysis for CC(=O)Oc1ccccc1C(=O)O

Generated from normalized retrosynthesis route data. Predictions require expert chemical review.

Visual style follows the bundled figure-style checklist: data-grounded labels, limited semantic colors, route-level claim consistency, and explicit uncertainty.

Routes analyzed5

Solved routes5

Top score0.998

Shortest solved route1

Route Ranking

Rank	Status	Score	Steps	Precursors	Starting materials
1	solved	0.998	1	2	CC(=O)OC(C)=O, O=C(O)c1ccccc1O
2	solved	0.998	1	2	CC(=O)Cl, O=C(O)c1ccccc1O
3	solved	0.998	1	2	CC(=O)O, O=C(O)c1ccccc1O
4	solved	0.998	1	2	CC(=O)O, O=C(O)c1ccccc1F
5	solved	0.994	2	2	CC(=O)OC(C)=O, O=C(OCc1ccccc1)c1ccccc1O

Interactive Retrosynthesis Knowledge Graph

Molecule Briefs

`CC(=O)Oc1ccccc1C(=O)O`

Role: target
Routes: 1, 2, 3, 4, 5
Stock: not a terminal precursor
Interpretation: Target molecule being disconnected into simpler purchasable or stock precursors.
Annotation: Example LLM molecule brief: this is a target in the displayed aspirin route set. The stock status is not a terminal precursor; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

`CC(=O)Oc1ccccc1C(=O)OCc1ccccc1`

Role: intermediate
Routes: 5
Stock: not a terminal precursor
Interpretation: Predicted synthetic intermediate; inspect functional groups, stereochemistry, and whether downstream disconnections are plausible.
Annotation: Example LLM molecule brief: this is a intermediate in the displayed aspirin route set. The stock status is not a terminal precursor; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

`CC(=O)Cl`

Role: stock precursor
Routes: 2
Stock: in stock
Interpretation: Terminal precursor found in the selected stock database; verify vendor, purity, price, and regulatory constraints.
Annotation: Example LLM molecule brief: this is a stock precursor in the displayed aspirin route set. The stock status is in stock; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

`CC(=O)O`

Role: stock precursor
Routes: 3, 4
Stock: in stock
Interpretation: Terminal precursor found in the selected stock database; verify vendor, purity, price, and regulatory constraints.
Annotation: Example LLM molecule brief: this is a stock precursor in the displayed aspirin route set. The stock status is in stock; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

`CC(=O)OC(C)=O`

Role: stock precursor
Routes: 1, 5
Stock: in stock
Interpretation: Terminal precursor found in the selected stock database; verify vendor, purity, price, and regulatory constraints.
Annotation: Example LLM molecule brief: this is a stock precursor in the displayed aspirin route set. The stock status is in stock; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

`O=C(O)c1ccccc1F`

Role: stock precursor
Routes: 4
Stock: in stock
Interpretation: Terminal precursor found in the selected stock database; verify vendor, purity, price, and regulatory constraints.
Annotation: Example LLM molecule brief: this is a stock precursor in the displayed aspirin route set. The stock status is in stock; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

`O=C(O)c1ccccc1O`

Role: stock precursor
Routes: 1, 2, 3
Stock: in stock
Interpretation: Terminal precursor found in the selected stock database; verify vendor, purity, price, and regulatory constraints.
Annotation: Example LLM molecule brief: this is a stock precursor in the displayed aspirin route set. The stock status is in stock; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

`O=C(OCc1ccccc1)c1ccccc1O`

Role: stock precursor
Routes: 5
Stock: in stock
Interpretation: Terminal precursor found in the selected stock database; verify vendor, purity, price, and regulatory constraints.
Annotation: Example LLM molecule brief: this is a stock precursor in the displayed aspirin route set. The stock status is in stock; confirm identity, purity, and route-specific functional-group compatibility before execution.
Query: PubChem

Target/intermediate Reaction Stock precursor Not in stock

Route 1

solved

Score0.998

Steps1

Stock precursors2

LLM Route Analysis

Route strategy: Example LLM route analysis: the aspirin target is disconnected at the aryl acetate bond, reducing the plan to salicylic-acid-derived material plus an acetyl donor. Route 1 uses acetic anhydride; this is chemically plausible, but the export alone does not validate conditions, impurity profile, or scale-up behavior.
Key disconnections: aryl acetate C(O)-O bond disconnection
salicylic acid phenol acylation in the forward direction
Reaction sequence: Confirm salicylic acid or the displayed salicylate precursor identity and availability.
Run the O-acylation with a literature-backed acetyl donor and monitor conversion by LCMS/HPLC.
Quench, isolate, and verify aspirin identity, residual salicylic acid, and hydrolysis level.
Conditions strategy: screen acetic anhydride loading, weak base or acid catalysis, and aqueous quench timing.
Yield outlook: A moderate-to-high step yield may be plausible for a simple phenolic acylation, but this example reports it as a planning estimate rather than an experimental fact.
Route risks: hydrolysis of aspirin during workup or storage
incomplete O-acylation leaving salicylic acid impurity
acid chloride or anhydride handling, heat release, and corrosive byproducts
Recommended next steps: search exact salicylic acid O-acylation precedent in SciFinder/Reaxys/internal ELN
check vendor, purity, and regulatory constraints for terminal precursors
run a small condition screen with HPLC assay before scale-up
Chemist verdict: go with verification: short and credible route, but conditions and analytical controls must be confirmed.

Step Evidence

Step 1: phenolic O-acylation / aryl acetate formation

0/100 coverage

No external evidence attached

No external evidence attached for this step.

Coverage is a transparent retrieval heuristic, not an experimental success probability. Verify cited records before execution.

Starting materials

CC(=O)OC(C)=OO=C(O)c1ccccc1O

Text outline

CC(=O)Oc1ccccc1C(=O)Omolecule

reaction template from usptoreaction
- CC(=O)OC(C)=Omolecule stock
- O=C(O)c1ccccc1Omolecule stock

Route 2

solved

Score0.998

Steps1

Stock precursors2

LLM Route Analysis

Route strategy: Example LLM route analysis: the aspirin target is disconnected at the aryl acetate bond, reducing the plan to salicylic-acid-derived material plus an acetyl donor. Route 2 uses acetyl chloride; this is chemically plausible, but the export alone does not validate conditions, impurity profile, or scale-up behavior.
Key disconnections: aryl acetate C(O)-O bond disconnection
salicylic acid phenol acylation in the forward direction
Reaction sequence: Confirm salicylic acid or the displayed salicylate precursor identity and availability.
Run the O-acylation with a literature-backed acetyl donor and monitor conversion by LCMS/HPLC.
Quench, isolate, and verify aspirin identity, residual salicylic acid, and hydrolysis level.
Conditions strategy: control exotherm, HCl capture, and moisture exclusion if acetyl chloride is selected.
Yield outlook: A moderate-to-high step yield may be plausible for a simple phenolic acylation, but this example reports it as a planning estimate rather than an experimental fact.
Route risks: hydrolysis of aspirin during workup or storage
incomplete O-acylation leaving salicylic acid impurity
acid chloride or anhydride handling, heat release, and corrosive byproducts
Recommended next steps: search exact salicylic acid O-acylation precedent in SciFinder/Reaxys/internal ELN
check vendor, purity, and regulatory constraints for terminal precursors
run a small condition screen with HPLC assay before scale-up
Chemist verdict: go with verification: short and credible route, but conditions and analytical controls must be confirmed.

Step Evidence

Step 1: phenolic O-acylation / aryl acetate formation

0/100 coverage

No external evidence attached

No external evidence attached for this step.

Coverage is a transparent retrieval heuristic, not an experimental success probability. Verify cited records before execution.

Starting materials

CC(=O)ClO=C(O)c1ccccc1O

Text outline

CC(=O)Oc1ccccc1C(=O)Omolecule

reaction template from usptoreaction
- CC(=O)Clmolecule stock
- O=C(O)c1ccccc1Omolecule stock

Route 3

solved

Score0.998

Steps1

Stock precursors2

LLM Route Analysis

Route strategy: Example LLM route analysis: the aspirin target is disconnected at the aryl acetate bond, reducing the plan to salicylic-acid-derived material plus an acetyl donor. Route 3 uses acetic acid with activation or dehydrating conditions; this is chemically plausible, but the export alone does not validate conditions, impurity profile, or scale-up behavior.
Key disconnections: aryl acetate C(O)-O bond disconnection
salicylic acid phenol acylation in the forward direction
Reaction sequence: Confirm salicylic acid or the displayed salicylate precursor identity and availability.
Run the O-acylation with a literature-backed acetyl donor and monitor conversion by LCMS/HPLC.
Quench, isolate, and verify aspirin identity, residual salicylic acid, and hydrolysis level.
Conditions strategy: treat direct acetic-acid esterification as lower confidence unless activation precedent is available.
Yield outlook: A moderate-to-high step yield may be plausible for a simple phenolic acylation, but this example reports it as a planning estimate rather than an experimental fact.
Route risks: hydrolysis of aspirin during workup or storage
incomplete O-acylation leaving salicylic acid impurity
acid chloride or anhydride handling, heat release, and corrosive byproducts
Recommended next steps: search exact salicylic acid O-acylation precedent in SciFinder/Reaxys/internal ELN
check vendor, purity, and regulatory constraints for terminal precursors
run a small condition screen with HPLC assay before scale-up
Chemist verdict: go with verification: short and credible route, but conditions and analytical controls must be confirmed.

Step Evidence

Step 1: phenolic O-acylation / aryl acetate formation

0/100 coverage

No external evidence attached

No external evidence attached for this step.

Coverage is a transparent retrieval heuristic, not an experimental success probability. Verify cited records before execution.

Starting materials

CC(=O)OO=C(O)c1ccccc1O

Text outline

CC(=O)Oc1ccccc1C(=O)Omolecule

reaction template from usptoreaction
- CC(=O)Omolecule stock
- O=C(O)c1ccccc1Omolecule stock

Route 4

solved

Score0.998

Steps1

Stock precursors2

LLM Route Analysis

Route strategy: Example LLM route analysis: the aspirin target is disconnected at the aryl acetate bond, reducing the plan to salicylic-acid-derived material plus an acetyl donor. Route 4 uses acetic acid with activation or dehydrating conditions; this is chemically plausible, but the export alone does not validate conditions, impurity profile, or scale-up behavior.
Key disconnections: aryl acetate C(O)-O bond disconnection
salicylic acid phenol acylation in the forward direction
Reaction sequence: Confirm salicylic acid or the displayed salicylate precursor identity and availability.
Run the O-acylation with a literature-backed acetyl donor and monitor conversion by LCMS/HPLC.
Quench, isolate, and verify aspirin identity, residual salicylic acid, and hydrolysis level.
Conditions strategy: treat direct acetic-acid esterification as lower confidence unless activation precedent is available.
Yield outlook: A moderate-to-high step yield may be plausible for a simple phenolic acylation, but this example reports it as a planning estimate rather than an experimental fact.
Route risks: hydrolysis of aspirin during workup or storage
incomplete O-acylation leaving salicylic acid impurity
acid chloride or anhydride handling, heat release, and corrosive byproducts
Recommended next steps: search exact salicylic acid O-acylation precedent in SciFinder/Reaxys/internal ELN
check vendor, purity, and regulatory constraints for terminal precursors
run a small condition screen with HPLC assay before scale-up
Chemist verdict: go with verification: short and credible route, but conditions and analytical controls must be confirmed.

Step Evidence

Step 1: phenolic O-acylation / aryl acetate formation

0/100 coverage

No external evidence attached

No external evidence attached for this step.

Coverage is a transparent retrieval heuristic, not an experimental success probability. Verify cited records before execution.

Starting materials

CC(=O)OO=C(O)c1ccccc1F

Text outline

CC(=O)Oc1ccccc1C(=O)Omolecule

reaction template from usptoreaction
- CC(=O)Omolecule stock
- O=C(O)c1ccccc1Fmolecule stock

Route 5

solved

Score0.994

Steps2

Stock precursors2

LLM Route Analysis

Route strategy: Example LLM route analysis: the aspirin target is disconnected at the aryl acetate bond, reducing the plan to salicylic-acid-derived material plus an acetyl donor. Route 5 uses acetic anhydride; this is chemically plausible, but the export alone does not validate conditions, impurity profile, or scale-up behavior.
Key disconnections: aryl acetate C(O)-O bond disconnection
salicylic acid phenol acylation in the forward direction
Reaction sequence: Confirm salicylic acid or the displayed salicylate precursor identity and availability.
Run the O-acylation with a literature-backed acetyl donor and monitor conversion by LCMS/HPLC.
Quench, isolate, and verify aspirin identity, residual salicylic acid, and hydrolysis level.
Conditions strategy: screen acetic anhydride loading, weak base or acid catalysis, and aqueous quench timing.
Yield outlook: A moderate-to-high step yield may be plausible for a simple phenolic acylation, but this example reports it as a planning estimate rather than an experimental fact.
Route risks: hydrolysis of aspirin during workup or storage
incomplete O-acylation leaving salicylic acid impurity
acid chloride or anhydride handling, heat release, and corrosive byproducts
Recommended next steps: search exact salicylic acid O-acylation precedent in SciFinder/Reaxys/internal ELN
check vendor, purity, and regulatory constraints for terminal precursors
run a small condition screen with HPLC assay before scale-up
Chemist verdict: go with verification: short and credible route, but conditions and analytical controls must be confirmed.

Step Evidence

Step 1: phenolic O-acylation / aryl acetate formation

0/100 coverage

No external evidence attached

No external evidence attached for this step.

Coverage is a transparent retrieval heuristic, not an experimental success probability. Verify cited records before execution.

Step 2: phenolic O-acylation / aryl acetate formation

0/100 coverage

No external evidence attached

No external evidence attached for this step.

Coverage is a transparent retrieval heuristic, not an experimental success probability. Verify cited records before execution.

Starting materials

CC(=O)OC(C)=OO=C(OCc1ccccc1)c1ccccc1O

Text outline

CC(=O)Oc1ccccc1C(=O)Omolecule

reaction template from usptoreaction
- CC(=O)Oc1ccccc1C(=O)OCc1ccccc1molecule
  - reaction template from usptoreaction
    - CC(=O)OC(C)=Omolecule stock
    - O=C(OCc1ccccc1)c1ccccc1Omolecule stock