Hydrochloric Acid → 5-(4-Chlorophenyl)-5-hydroxypentanoic acid

HRID 1904616Notes

Reaction equation

HRID 1904616 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[BH4-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:7])[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27337165-(4-Chlorophenyl)-5-oxopentanoic acidHCID 4311764Sodium borohydride

Product 1

HCID 145768835-(4-Chlorophenyl)-5-hydroxypentanoic acidYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 10.6 g of 4-(4-chlorobenzoyl)butanoic acid and 1.9 g of sodium hydroxide in 50 ml of water was added under ice-cooling 2.7 g of sodium borohydride portionwise over 35 minutes, and the mixture was stirred at room temperature for 24 hours. The mixture was made acidic with diluted hydrochloric acid under ice-cooling, extracted with ether. The ether extract was washed with water and dried. After removal of the solvent, the residue was recrystallized from a mixture of ethyl acetate-n-hexane to give 7.50 g of 5-(4-chlorophenyl)-5-hydroxypentanoic acid as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. customdried
  6. customAfter removal of the solvent
  7. customthe residue was recrystallized from a mixture of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-5991b39119094401bb1201f1408f526a
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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