2-Phenylpropionic acid → Methyl alpha-methylbenzeneacetate

HRID 1058177Notes

Reaction equation

HRID 1058177 reaction equation
[CH2:1]1CCN2C(=NCCC2)CC1.[C:12]1([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl.O>[C:12]1([CH:18]([CH3:22])[C:19]([O:21][CH3:1])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 102962-Phenylpropionic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 569653Methyl alpha-methylbenzeneacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

DBU (2.03 g, 13.3 mmol) was added to a mixture of 2-phenylpropionic acid (2.0 g, 13.3 mmol) in DMC (20 mL) and the resulting mixture was heated to reflux (90° C.) for 5 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 (2×50 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give methyl 2-phenylpropionate 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 (2×50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ea4be6d6aa0d4446a9e96d74c2562758
Source dataset
uspto-grants-2003_02
Patent number
US06515167B1

Reaction notes

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