Phenol → Carbamic acid, phenyl-, phenyl ester (9CI)

HRID 258067Notes

Reaction equation

HRID 258067 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[F-].[Cs+]>[C:1]1([NH:7][C:8](=[O:9])[O:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 7672Phenyl isocyanate

Product 1

HCID 78644Carbamic acid, phenyl-, phenyl ester (9CI)Yield 98.6%

Reagents, catalysts & solvents 1

HCID 25953Cesium fluorideCatalyst

Conditions

Temperature
105 °C

Procedure

1.28 g (8.4 mmol) of cesium fluoride was weighed into a flask and dried under a reduced pressure at 130° C. for 30 minutes. 50 g (0.42 mol) of phenyl isocyanate and 39.5 g (0.42 mol) of phenol were added thereto with stirring at 105° C. for 10 minutes, followed by the removal of an unreacted raw material at a reduced pressure. Thus, 88.3 g of phenyl N-phenylcarbamate having a melting point of 123° to 124° C. was obtained at a yield of 93.1%.

Workup

  1. customdried under a reduced pressure at 130° C. for 30 minutes
  2. customfollowed by the removal of an unreacted raw material at a reduced pressure

Sources & evidence

ORD record
ord-076acbc8828540c1bce24bd2223deb3c
Source dataset
uspto-grants-1993_11
Patent number
US05264572

Reaction notes

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