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

HRID 1080502Notes

Reaction equation

HRID 1080502 reaction equation
[I: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][I:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 113143824-(4Iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetic acid

Product 1

HCID 222227064-(1-Hydroxy-4-iodobutyl)-alpha,alpha-dimethylphenylacetic acidYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 50 mg of 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetic acid, prepared in accordance with Example 3, 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 removed in vacuo. The concentrate was extracted with EtOAc. The organics were dried over Na2SO4, filtered, and concentrated to afford 40 mg of 4-(1-hydroxy-4-iodobutyl)-α,α-dimethylphenylacetic acid.

Workup

  1. customthe methanol 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-2458dc47a36a4626b720bd387d85a290
Source dataset
uspto-grants-1996_12
Patent number
US05581011

Reaction notes

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