Water → (R)-2-Phenylbutan-1-ol

HRID 636757Notes

Reaction equation

HRID 636757 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C@@H:13]([CH2:17][CH3:18])[C:14](O)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[K+]>C1COCC1>[C:7]1([C@@H:13]([CH2:17][CH3:18])[CH2:14][OH:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 7853302-Phenylbutyric acid, (R)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 5325939(R)-2-Phenylbutan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 2.3 gm of LAH (60.6 mmol) in 70 mL of THF was slowly added a solution of 5 gm of (R)-(−)-2-phenylbutyric acid (30.45 mmol, Aldrich) in 30 mL of THF. The reaction mixture was heated to 60° C. for 3 hr. The reaction was cooled to 0° C. and to it was successively added 2 mL of water, 2 mL of 1N KOH and 2 mL of water. The aluminum salts were removed by filtration and washed with 100 mL of ethylacetate. The filtrate was dried over MgSO4, filtered and concentrated to give the title compound which was used without purification.

Workup

  1. temperatureThe reaction was cooled to 0° C. and to it
  2. customThe aluminum salts were removed by filtration
  3. washwashed with 100 mL of ethylacetate
  4. dry with materialThe filtrate was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b916815584f14b6080ddb315ae39c57b
Source dataset
uspto-grants-2001_02
Patent number
US06194458B1

Reaction notes

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