3-Chloro-4-hydroxybenzaldehyde → Benzonitrile, 3-chloro-4-hydroxy-

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[Cl-].O[NH3+:13]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:13]

Participants

Reactant 2

HCID 170223-Chloro-4-hydroxybenzaldehyde

HCID 21645Hydroxylamine HCl

Product 1

HCID 2735739Benzonitrile, 3-chloro-4-hydroxy-

Procedure

The title compound was prepared from 3-chloro-4-hydroxybenzaldehyde and hydroxyl ammonium chloride, using the same method as that described for preparation 70. The title compound was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate, 100:0 to 90:10, to afford the title compound as a white solid in 76% yield.

Workup

customthat described for preparation 70
customThe title compound was purified by column chromatography on silica gel
washeluting with pentane

Sources & evidence

ORD record: ord-6b4d3adad6aa446198f258bdd7b98692
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207198B2

Reaction notes

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