Acetyl chloride → 1-Methyl 2-carboxybenzenepropanoate

HRID 1381614Notes

Reaction equation

HRID 1381614 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2].[C:15](OC(=O)C)(=O)C.C(Cl)(=O)C>ClCCl>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 2262943-(2-Carboxyphenyl)propionic acid

Product 1

HCID 117904221-Methyl 2-carboxybenzenepropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-carboxybenzenepropanoic acid (9.7 g., 0.05 mole), acetic anhydride (15.5 g., 0.15 mole) and acetyl chloride (0.5 g) in dichloromethane (200 ml) was boiled at reflux under nitrogen for 16 hr. The solvents were removed at high vacuum and the residual cyclic anhydride was heated at reflux with methanol (250 ml) for 2 hrs. Evaporation of solvent gave the sub-title compound as an oil which crystallised with petroleum ether (b.p. 60°-80°) to a solid (6.3 g) mp 76°-79°. This was further purified by continuous extraction of the crude product with boiling petroleum (b.p. 40°-60°) in a Soxhlet apparatus. The pure compound, mp 79°-81° separated from the extracts on cooling.

Workup

  1. temperatureat reflux under nitrogen for 16 hr
  2. customThe solvents were removed at high vacuum
  3. temperaturethe residual cyclic anhydride was heated
  4. temperatureat reflux with methanol (250 ml) for 2 hrs
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-e166cd7f72b14d9eb0472c3d076836f3
Source dataset
uspto-grants-1989_02
Patent number
US04803225

Reaction notes

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