Methyl Glycolate → Phenylacetic Acid

HRID 1989874Notes

Reaction equation

HRID 1989874 reaction equation
O[CH2:2][C:3]([O:5]C)=[O:4].ClC([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C(Cl)=O>C1COCC1.O>[C:12]1([CH2:2][C:3]([OH:5])=[O:4])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 66774Methyl GlycolateHCID 102902Chloro(phenyl)acetyl chloride

Product 1

HCID 999Phenylacetic AcidYield 166.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-hydroxyacetate (0.2 mol) in THF (100 ml) was stirred on an ice bath. 2-Chloro-2-phenylacetyl chloride (0.132 mol) was added dropwise. The mixture was stirred overnight, poured out in water and then stirred for 20 minutes. The mixture was extracted with DEPE. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 30 g of benzeneacetic acid, α-chloro-, 2-methoxy-2-oxoethyl ester (intermediate 43).

Workup

  1. stirringThe mixture was stirred overnight
  2. stirringstirred for 20 minutes
  3. extractionThe mixture was extracted with DEPE
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fb5ea9c8707543fe946ce9b5dc55e65d
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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