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

HRID 432052Notes

Reaction equation

HRID 432052 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

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 178516824HCID 178516824, compound

Product 1

HCID 182159Benzeneacetic acid, 2-hydroxy-alpha-oxo-, methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 1 hour
  3. distillationThe solvent is distilled off under reduced pressure
  4. additionthe residue is poured into water
  5. extractionthe product is extracted with diethyl ether
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-3ea6f16492de4ba69a52bca564e98c13
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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