Benzene → Phenyl isocyanate

HRID 247004Notes

Reaction equation

HRID 247004 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:7]=[C:8]=[O:9]>C(#N)C>[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 241BenzeneHCID 105034Isocyanate

Product 1

HCID 7672Phenyl isocyanate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In the present invention, benzene is oxidized in acetonitrile to form a radical cation. The isocyanate anion (solubilized by the 18-crown-6 polyether) then attacks the activated ring to give a phenyl isocyanate radical which then loses a proton to give phenyl isocyanate. The 18-crown-6 acts as a solid to liquid phase transfer catalyst bringing the insoluble KOCN into the acetonitrile solution. A schematic is shown below.

Workup

  1. customto form a radical cation

Sources & evidence

ORD record
ord-b3acc75d2f4548e6b3c143dc05c1fcb5
Source dataset
uspto-grants-1987_11
Patent number
US04705609

Reaction notes

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