Hydrochloric Acid → 1-(4-Isobutylphenyl)hexan-1-ol

HRID 1741817

Reaction equation

HRID 1741817 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[BH4-].[Na+].Cl>CC(O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 108790194'-Isobutylhexanophenone

Product 1

HCID 109334301-(4-Isobutylphenyl)hexan-1-olYield 88%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4'-isobutylhexanophenone (10.5 g) in 2-propanol (60 ml) was added sodium borohydride (2.05 g), and the mixture was stirred at 50° C. for 6 hours. The mixture was poured into ice water and acidified with 6N hydrochloric acid. The aqueous solution was extracted with ethyl acetate and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated to give 1-(4-isobutylphenyl)hexan-1-ol (9.32 g) as a colorless oil.

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-a1be9c664a39446897f23a19421181ab
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Linked notes

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