Hydrochloric Acid → 4-(4-Cyclohexylphenyl)-4-oxobutanoic acid

HRID 861864Notes

Reaction equation

HRID 861864 reaction equation
[CH:1]1([C:7]2[CH:21]=[CH:20][C:10]([C:11]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.Cl>CO.[OH-].[K+]>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[CH:20][CH:21]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14903180HCID 14903180, compound

Product 1

HCID 1618624-(4-Cyclohexylphenyl)-4-oxobutanoic acidYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

To a solution of ethyl 3-(4-cyclohexylbenzoyl)propionate (19.6 g) in methanol (150 ml), 2N KOH (102 ml) was added, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured into water (200 ml), acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was evaporated off, to yield 3-(4-cyclohexylbenzoyl)propionic acid (10.8 g, 61%), which was then recrystallized from isopropyl ether to yield colorless prisms having a melting point of 140°-141° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customafter which the solvent was evaporated off

Sources & evidence

ORD record
ord-3410177dbdfc4c0e8d13c898681659bf
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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