Methanol → Benzeneacetic acid, 2-hydroxy-alpha-oxo-, methyl ester

Reaction equation

[C:1](Cl)(=[O:3])C.C[OH:6].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[C:8]1=NO>CC(C)=O>[OH:7][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9](=[O:16])[C:8]([O:3][CH3:1])=[O:6]

Participants

Procedure

27 g of acetyl chloride (0.344 mol) are added dropwise to a mixture of 245 ml of methanol and 245 ml of acetone. 20 g (0.123 mol) of benzofuran-2,3-dione 2-oxime are dissolved in this mixture and the mixture is subsequently heated under reflux for 1 hour. The solvent is distilled off under reduced pressure, the residue is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 20.8 g of crude product which, according to HPLC, contains 92.4% methyl 2-hydroxyphenylglyoxylate of log p=1.87.