Benzene → Veratryl chloride

HRID 1704233Notes

Reaction equation

HRID 1704233 reaction equation
CO[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[CH2:11]=[O:12].[ClH:13].[CH:14]1C=CC=CC=1>>[CH3:11][O:12][C:3]1[CH:8]=[CH:7][C:6]([CH2:14][Cl:13])=[CH:5][C:4]=1[O:9][CH3:10]

Participants

5

Reactant 4

HCID 241Benzene2×HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7043Veratrole

Product 1

HCID 81740Veratryl chloride

Procedure

180 kg. of 1,2-dimethoxy-benzene are chloromethylated with 44 kg. of paraformaldehyde and 280 kg. of concentrated hydrochloric acid at 48°-70° C in benzene as medium. The benzene solution of the 1,2-dimethoxy-4-chloromethyl-benzene thus obtained is heated with an aqueous solution of 105 kg. of sodium cyanide in the presence of fatty alcohol sulfonate emulsifier, under stirring. After removing the solvent 200-210 kg. of crude 3,4-dimethoxy-benzene cyanide are obtained, which may be purified by means of fractionating in vacuo in the presence of 3-5 kg. of triethylamine. At 110° to 168° C per 20 Hgmm (vapour temperature) 54-58 kg. of a forerun whereafter at 168°-196° C/5-8 Hgmm. 102-106 kg. of 3,4-dimethoxy-benzylcyanide as main fraction are obtained. The forerun contains predominantly 1,2-dimethoxy-benzene- and a small amount of 3,4-dimethoxy-benzyl cyanide.

Workup

  1. customat 48°-70° C

Sources & evidence

ORD record
ord-2c72591accf9422d8ce731ff44d7dbc2
Source dataset
uspto-grants-1978_11
Patent number
US04126615

Reaction notes

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