Methanol → Methyl phenylacetate

HRID 1957277Notes

Reaction equation

HRID 1957277 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11]O>>[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 999Phenylacetic Acid

Product 1

HCID 7559Methyl phenylacetate

Procedure

Dissolved 13 g (0.1 mol) of phenylacetic acid in 500 ml of anhydrous methanol. Introduced HC1 gas, while refluxing for 3 hours. The solvent was then removed by evaporation. Dissolved the ester in benzene, which was successively washed with water and 10% NaOH. The organic layer was dehydrated with anhydrous magnesium sulfate. The solvent was again removed by evaporation. Methyl phenylacetate was finally purified by column chromatography employing silica gel chloroform system. The solvent was removed by evaporation to yield yellowish liquid. Yield, 6 g (40% ).

Workup

  1. additionIntroduced HC1 gas
  2. temperaturewhile refluxing for 3 hours
  3. customThe solvent was then removed by evaporation
  4. dissolutionDissolved the ester in benzene, which
  5. washwas successively washed with water and 10% NaOH
  6. customThe solvent was again removed by evaporation
  7. customMethyl phenylacetate was finally purified by column chromatography
  8. customThe solvent was removed by evaporation
  9. customto yield yellowish liquid
  10. customYield

Sources & evidence

ORD record
ord-e6f37a4998ac4c5395fac5aefeeeb292
Source dataset
uspto-grants-1998_07
Patent number
US05783605

Reaction notes

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