Methane → Cyclohexyl isocyanate

HRID 279797

Reaction equation

HRID 279797 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([OH:18])C2C(=CC=CC=2)C=CC=1.C>[I-].C([N+](CC)(CC)CC)C.[Rh]>[CH:1]1([N:7]=[C:8]=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 297MethaneHCID 70051-NaphtholHCID 7965Cyclohexylamine

Product 1

HCID 18502Cyclohexyl isocyanate

Reagents, catalysts & solvents 2

HCID 6225Tetraethylammonium IodideCatalystHCID 23948RhodiumCatalyst

Procedure

The carbonylation reaction is conducted in the same manner as in Example 1 except that 25 mmol of cyclohexylamine, 86 g of α-naphthol, 1.5 g of Rh/C having 5% Rh carried on activated charcoal and 1 mmol of tetraethylammonium iodide are employed. As a result, the yields of cyclohexyl isocyanate and α-naphthyl cyclohexyl carbamate are 58% and 10%, respectively.

Workup

  1. customThe carbonylation reaction

Sources & evidence

ORD record
ord-df5d85d8c97f4f9bbfa76d696c7c7942
Source dataset
uspto-grants-1986_05
Patent number
US04587056

Linked notes

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