Hydrochloric Acid → 4-(1-Hydroxy-4-chlorobutyl)-alpha,alpha-dimethylphenylacetic acid

HRID 896820Notes

Reaction equation

HRID 896820 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[BH4-].[Na+].Cl>CO>[OH:6][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)[CH2:4][CH2:3][CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

Product 1

HCID 222694034-(1-Hydroxy-4-chlorobutyl)-alpha,alpha-dimethylphenylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 50 mg of 4-(4-chloro-1-oxobutyl)-α,α-dimethylphenylacetic acid in 3 mL of methanol was added 50 mg of NaBH4. The mixture was stirred for 30 minutes, acidified with 2N HCl, and the methanol was removed in vacuo. The concentrate was extracted with EtOAc. The organics were dried over Na2SO4, filtered, and concentrated to afford 4-(1-hydroxy-4-chlorobutyl)-α,α-dimethylphenylacetic acid.

Workup

  1. customthe methanol was removed in vacuo
  2. extractionThe concentrate was extracted with EtOAc
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e954578273ff4a0ead062439d91dd5ec
Source dataset
uspto-grants-2005_07
Patent number
US06919458B2

Reaction notes

Loading…