Hydrochloric Acid → Phenylacetic Acid

HRID 27809

Reaction equation

HRID 27809 reaction equation
[C:1]1([CH2:7][C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C)([O-])=O>[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 60999Benzyl phenylacetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 999Phenylacetic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A mixture of benzyl phenylacetate (218 mg), methylene chloride (2 ml), aluminum chloride (357 mg), and nitromethane (1 ml) is stirred for 1 hour under ice cooling. The mixture is acidified with cold dilute hydrochloric acid and extracted with methylene chloride. The organic layer is extracted again with 5% aqueous sodium hydrogen carbonate solution. The aqueous extract is acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and concentrated to give phenylacetic acid (114 mg) melting at 77° C. Yield: 87%.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe organic layer is extracted again with 5% aqueous sodium hydrogen carbonate solution
  3. extractionThe aqueous extract
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-052b6611baf54db8aba7f13890d7e39c
Source dataset
uspto-grants-1980_09
Patent number
US04223132

Linked notes

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