(+-)-alpha-Pinene → 1-Chloroethyl isocyanate

HRID 848049Notes

Reaction equation

HRID 848049 reaction equation
[Cl:1][CH:2]([NH:4][C:5](Cl)=[O:6])[CH3:3].CC1C2C(C)(C)C(C2)CC=1>>[Cl:1][CH:2]([N:4]=[C:5]=[O:6])[CH3:3].[CH:2]([N:4]=[C:5]=[O:6])=[CH2:3]

Participants

4

Reactant 2

HCID 6654(+-)-alpha-PineneHCID 12573467(1-Chloroethyl)carbamyl chloride

Product 2

HCID 77094Vinyl isocyanateHCID 125734821-Chloroethyl isocyanateYield 23%

Procedure

A mixture of 160 parts of 1-chloroethylcarbamic acid chloride and 537 parts of α-pinene is heated at from 124° to 105° C. in the course of 2 hours, whilst stirring, and the reaction mixture is then subjected to fractional distillation. A total of 27.6 parts (23% of theory) of 1-chloroethyl isocyanate of boiling point 92° C./1013 mbar and 34.6 parts of vinyl isocyanate of boiling point 38.5° C./1013 mbar is obtained.

Workup

  1. temperatureis heated at from 124° to 105° C. in the course of 2 hours
  2. distillationthe reaction mixture is then subjected to fractional distillation

Sources & evidence

ORD record
ord-a73b23cdc16845f6a9d5c0eac9fbf287
Source dataset
uspto-grants-1981_10
Patent number
US04294773

Reaction notes

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