4-Aminophenol → HCID 14745381, compound

HRID 1587270Notes

Reaction equation

HRID 1587270 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[OH:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>CN(C)C=O>[OH:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:2](=[O:3])[O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 14745381HCID 14745381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.3 g (0.02 mol) of 2,2,2-trichloroethyl chloroformate are dissolved in 20 ml of DMF (dimethyl formamide) and added dropwise to a solution of 10.9 g (0.1 mol) of 4-hydroxyaniline in 100 ml of DMF. After the mixture has been stirred for a further hour at room temperature, it is poured into ice water, acidified and filtered with suction, and the material filtered off is washed with water. The product is recrystallized from toluene using activated charcoal. 2.3 g of a substance of melting point 134° C. are obtained; 1H NMR: --NH-- 9.17 ppm (s, 1H), --CH2 4.9 ppm (s, 2H), --OH (+H2O) 3.31 ppm (s), aromatics 6.67 ppm (d, 2H) 7.27 ppm (d, 2H).

Workup

  1. filtrationfiltered with suction
  2. filtrationthe material filtered off
  3. washis washed with water
  4. customThe product is recrystallized from toluene using activated charcoal
  5. custom2.3 g of a substance of melting point 134° C. are obtained

Sources & evidence

ORD record
ord-f8645982a6bc4bbd9a5ea9ef5805a277
Source dataset
uspto-grants-1993_06
Patent number
US05217843

Reaction notes

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