5-Oxo-5-phenylvaleronitrile → 5-Hydroxy-5-phenylvaleronitrile

HRID 27915Notes

Reaction equation

HRID 27915 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][CH2:11][C:12]#[N:13]

Participants

3

Reactant 2

HCID 3126635-Oxo-5-phenylvaleronitrileHCID 4148881Lithium borohydride

Product 1

HCID 141722705-Hydroxy-5-phenylvaleronitrile

Procedure

A mixture of 41 g. (0.25 mole) of 5-hydroxy-5-phenylvaleronitrile, obtained from 4-benzoylbutyronitrile by lithium borohydride reduction by the procedure of Colonge et. al., Bull. Soc. Chem. France, 2005-2011 (1966); Chem. Abstr., 65, 18547d (1966), and 0.30 mole of potassium hydroxide in 200 ml. of water was heated at reflux for eight hours. The mixture was cooled to room temperature and neutralized with 10 M hydrochloric acid, saturated with sodium chloride and extracted with ether several times. The extracts were washed with water, dried (Na2SO4) and the ether evaporated to obtain dl-5-phenyl-5-hydroxyvaleric acid lactone which was recrystallized from dilute alcohol, M.P. 62.5° C., 79% yield.

Workup

  1. additionA mixture of 41 g

Sources & evidence

ORD record
ord-4d99f935a6a643769a5256f72e09b8f7
Source dataset
uspto-grants-1980_09
Patent number
US04224329

Reaction notes

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