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

HRID 2244772Notes

Reaction equation

HRID 2244772 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-53d7468526f24656971787226d8f0626
Source dataset
uspto-grants-2010_03
Patent number
US07678915B2

Reaction notes

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