Benzene → 4-Phenylbutyric Acid

HRID 842344Notes

Reaction equation

HRID 842344 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:10])[O:9][CH2:8][CH2:7][CH2:6]1.[OH-].[Na+].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([CH2:8][CH2:7][CH2:6][C:5]([OH:9])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 7302Gamma-ButyrolactoneHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 47754-Phenylbutyric AcidYield 93.7%

Conditions

Temperature
50 °C

Procedure

Powdered aluminum chloride (200 g) was added to benzene (400 g) and stirred for 10 min at 50° C. Butyrolactone (86 g) was added in small portions. The temperature was maintained between 50 and 60° C. for 90 min and then the reaction mixture was added, with stirring, to a mixture of ice and 5% sodium hydroxide. The temperature was maintained below 35° C. and the pH was maintained between 9 and 9.5 for 2 hr. The mixture was filtered under vacuum. Phenylbutyric acid was precipitated from the aqueous fraction by the addition of ice and hydrochloric acid. Crude (93.7%-94.3%) 4-phenylbutyric acid was isolated by vacuum filtration.

Workup

  1. temperatureThe temperature was maintained between 50 and 60° C. for 90 min
  2. additionthe reaction mixture was added
  3. temperatureThe temperature was maintained below 35° C.
  4. temperaturethe pH was maintained between 9 and 9.5 for 2 hr
  5. filtrationThe mixture was filtered under vacuum
  6. customPhenylbutyric acid was precipitated from the aqueous fraction by the addition of ice and hydrochloric acid

Sources & evidence

ORD record
ord-d5d654553ef342dc9d698e35e1a5b6f9
Source dataset
uspto-grants-2002_04
Patent number
US06372938B1

Reaction notes

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