Water → Benzenebutanol

HRID 1613706Notes

Reaction equation

HRID 1613706 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C(OCC)C>[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 47754-Phenylbutyric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 76889BenzenebutanolYield 83.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 7.9 g (0.21 mole) of lithium aluminum hydride (Aldrich) in 350 ml of dry ethyl ether was added dropwise a solution of 32.8 g (0.2 mole) of 4-phenylbutyric acid (Aldrich) in 250 ml of dry ethyl ether. The reaction mixture was stirred at ambient temperature for 2 hr, treated successively with 8 ml of water, 25 ml of a 15% sodium hydroxide solution and 8 ml of water, and filtered through Celite®. The filtrate was washed successively with water (200 ml), twice with 300 ml portions of sodium bicarbonate solution, 300 ml of water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 25.0 g (83%) of colorless oil.

Workup

  1. filtrationfiltered through Celite®
  2. washThe filtrate was washed successively with water (200 ml), twice with 300 ml portions of sodium bicarbonate solution, 300 ml of water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f53d845f4fa740ba8992f5937c7b104e
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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