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

HRID 1281108Notes

Reaction equation

HRID 1281108 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, prepared in accordance with Example 4, in 3 mL of methanol is added 50 mg of NaBH4. The mixture is stirred for 30 minutes, acidified with 2N HCl, and the methanol is removed in vacuo. The concentrate is extracted with EtOAc. The organics are dried over Na2SO4, filtered, and concentrated to afford 4-(1-hydroxy-4-chlorobutyl)-α,α-dimethylphenylacetic acid.

Workup

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

Sources & evidence

ORD record
ord-a03cfda88bfe4f0199fda2cfe1403c89
Source dataset
uspto-grants-2002_09
Patent number
US06452011B1

Reaction notes

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