2-Aminophenol → 4-Isocyanatophenol

HRID 2102758Notes

Reaction equation

HRID 2102758 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:11]=[CH:10]C=[CH:8][C:7]=1O.[C:13](OCC)(=[O:15])C>C1(C)C=CC=CC=1>[N:5]([C:6]1[CH:11]=[CH:10][C:1]([OH:2])=[CH:8][CH:7]=1)=[C:13]=[O:15]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 6371PhosgeneHCID 8857Ethyl Acetate

Product 1

HCID 124834764-Isocyanatophenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of phosgene (20% in Toluene, 24 mL, 45.9 mmol) (Aldrich) in ethyl acetate (25 mL) at 0° C. was added aminophenol (0.5 g, 4.59 mmol) (Aldrich). The reaction mixture was stirred at 0° C. for 30 minutes and then heated at 80° C. for 3 hours. The mixture was cooling down to room temperature to give crude 4-isocyanato-phenol as 0.18 M solution in toluene and used for the next step without further purification.

Workup

  1. temperatureheated at 80° C. for 3 hours
  2. temperatureThe mixture was cooling down to room temperature

Sources & evidence

ORD record
ord-c097451571db4f0f9f0c7e30225433c4
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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