Phenylacetic Acid → Methyl phenylacetate

HRID 1058176Notes

Reaction equation

HRID 1058176 reaction equation
[CH2:1]1CCN2C(=NCCC2)CC1.[C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl.O>[C:12]1([CH2:18][C:19]([O:21][CH3:1])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 999Phenylacetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 7559Methyl phenylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

DBU (3.35 g, 22.0 mmol) was added to a mixture of phenylacetic acid (3.0 g, 22.0 mmol) in DMC (30 mL) and the resulting mixture was heated to reflux (90° C.) for 24 hours. The reaction mixture was cooled to ambient temperature and diluted with CH2Cl2 (50 mL) and water (40 mL). The organic layer was separated and washed in sequence with 2 M HCl (2×40 mL), saturated aqueous NaHCO3 (40 mL) and water (2×40 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give methyl phenylacetate as an oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customThe organic layer was separated
  4. washwashed in sequence with 2 M HCl (2×40 mL), saturated aqueous NaHCO3 (40 mL) and water (2×40 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fe1a429b411f4775ac6b872b11d7fb3c
Source dataset
uspto-grants-2003_02
Patent number
US06515167B1

Reaction notes

Loading…