Water → 3-Benzyloxyphenylacetonitrile

HRID 1288246Notes

Reaction equation

HRID 1288246 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.CCOCC>CS(C)=O>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH2:15][C:1]#[N:2])[CH:17]=[CH:18][CH:19]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 131734901-(Benzyloxy)-3-(chloromethyl)benzene

Product 1

HCID 5198313-Benzyloxyphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of sodium cyanide (5.9 g.) in dimethyl sulphoxide (40 ml.) was treated with 3-benzyloxybenzyl chloride (23.2 g.) and the reaction mixture stirred and maintained at 60° for 1 hour. The mixture was poured into water and the product was isolated with ether in the usual manner to give 3-benzyloxyphenylacetonitrile, b.p. 162°-166°/0.55 mm.

Workup

  1. temperaturemaintained at 60° for 1 hour

Sources & evidence

ORD record
ord-d80b44e9bbcd4bf387415ded71bea0c3
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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