Water → 1-Phenyl-1-butanol

HRID 2293661Notes

Reaction equation

HRID 2293661 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[C:6]1([CH:1]([OH:5])[CH2:2][CH2:3][CH3:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10315ButyrophenoneHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 953721-Phenyl-1-butanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirring solution of 890 mg of commercially available butyrophenone in 30 mL of diethyl ether under an argon atmosphere at 0° C. is slowly added 250 mg of lithium aluminum hydride in portions. After 2 hours the grey suspension is slowly treated with 0.25 mL of water followed by 1.10 mL of 1N sodium hydroxide. After 0.5 hours the resulting whim precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings. The filtrate is concentrated under reduced pressure to afford 0.90 g of the title product as a clear, colorless oil. This product may be used directly in the next reaction without further purification.

Workup

  1. customat 0° C.
  2. filtrationAfter 0.5 hours the resulting whim precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-829e77f419294ffdae2d7583067baff8
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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