4-Nitrobenzaldehyde → 1-(dichloromethyl)-4-nitrobenzene

HRID 442071Notes

Reaction equation

HRID 442071 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7](C=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([Cl:15])([Cl:14])=O>C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:12]([Cl:15])[Cl:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 6371Phosgene

Product 1

HCID 7286831-(dichloromethyl)-4-nitrobenzeneYield 107.4%

Reagents, catalysts & solvents 1

HCID 13097Triphenylphosphine OxideCatalyst

Procedure

151 g (1 mol) of p-nitrobenzaldehyde and 5 g (0.018 mol) of triphenylphosphine oxide are treated, in the tube reactor described above, at a temperature of 120° to 140° C, for 6 hours with 80 g (0.8 mol) of phosgene gas per hour. At the end of the reaction time the increased in weight was 53 g (calculated 55 g). Vacuum distillation of the resulting crude product gave, in a boiling range of 100° to 110° C/1.5 mm Hg, 177 g (86% of theory) of p-nitrobenzal chloride with a melting point of 44° to 46° C.

Workup

  1. customat a temperature of 120° to 140° C
  2. temperatureAt the end of the reaction time the increased in weight
  3. distillationVacuum distillation of the resulting crude product

Sources & evidence

ORD record
ord-5afd78d135814468b02bb5d060ec3d7b
Source dataset
uspto-grants-1977_08
Patent number
US04044060

Reaction notes

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