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

HRID 249184

Reaction equation

HRID 249184 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 combined 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 combined organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-3c9269b25b7b474dbd8fb82ea98e1513
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Linked notes

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