Hydrochloric Acid → 4-Isocyanato-1,2-dimethoxybenzene

HRID 1729986Notes

Reaction equation

HRID 1729986 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.Cl.[C:13](Cl)(Cl)=[O:14]>ClC1C=CC=CC=1>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([N:1]=[C:13]=[O:14])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 227703,4-Dimethoxyaniline

Product 1

HCID 35178104-Isocyanato-1,2-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

A solution of 0.163 m of 4-aminoveratrole in 250 ml of chlorobenzene was treated with excess HCl gas resulting in a heavy precipitate. The mixture was refluxed and treated with a stream of phosgene for 1/2 hr (50 g, 0.49 m). After refluxing an additional 1/2 hr chlorobenzene was evaporated in vacuo. Distillation of the residue afforded 23 g (79%) b.p. 145°-150° C, 17-18 mm.

Workup

  1. customresulting in a heavy precipitate
  2. temperatureThe mixture was refluxed
  3. customwas evaporated in vacuo
  4. distillationDistillation of the residue
  5. customafforded 23 g (79%) b.p. 145°-150° C, 17-18 mm

Sources & evidence

ORD record
ord-d725e06bc5aa48f09c57f842cff95221
Source dataset
uspto-grants-1976_11
Patent number
US03991064

Reaction notes

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