Hydrogen Cyanide → 4-methoxybenzoyl cyanide

HRID 1834156Notes

Reaction equation

[CH3:1][N:2](C)CC1C=CC=CC=1.[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.C#N>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([C:1]#[N:2])=[O:18])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 135 g (1 mole) of dimethylbenzylamine in 100 ml of toluene was added dropwise, at -20° C, while cooling, in the course of 30 minutes to a mixture of 170 g (1 mole) of para-methoxybenzoyl chloride and 50 g of anhydrous hydrocyanic acid in 400 ml of toluene at such a rate that the internal temperature did not rise above -20° C during the addition. When the addition was complete, the mixture was stirred for a further 10 minutes at -20° C and excess hydrocyanic acid was then distilled, under a waterpump vacuum, into a cooled receiver. The residue was recrystallized from a mixture of benzene and ligroin. In this way 128 g (77% of theory) of para-methyoxybenzoyl cyanide with a melting point of 63° C were obtained.

Workup

additiondid not rise above -20° C during the addition
additionWhen the addition
distillationexcess hydrocyanic acid was then distilled, under a waterpump vacuum, into a cooled receiver
customThe residue was recrystallized from a mixture of benzene and ligroin

Sources & evidence

ORD record: ord-ca5db733ee2143799c204677013bbf02
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04069252

Reaction notes

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