4-Aminophenol → Benzyl (4-hydroxyphenyl)carbamate

HRID 1900876Notes

Reaction equation

HRID 1900876 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>C1COCC1>[CH2:5]([O:4][C:2]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 10387Benzyl chloroformate

Product 1

HCID 293061Benzyl (4-hydroxyphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzyl chloroformate (14 ml) in THF (30 ml) was added dropwise over 40 minutes to an ice-cold solution of 4-aminophenol (11 g) in THF (500 ml), the temperature of the reaction mixture being maintained at 0°-5° C. On completion of the addition, the reaction mixture was stirred at ambient temperature for 2 hours and the precipitated solid was collected and crystallised from a mixture of ethyl acetate and hexane to give 4-benzyloxycarbonylaminophenol (11.3 g) as a white solid: m.p. 153°-154° C.; Elemental Analysis: calculated for C14H13NO3 : C, 69.1%; H, 5.4%; N, 5.8%; found: C, 69.3%; H, 5.3%; N, 5.8%.

Workup

  1. temperaturethe temperature of the reaction mixture being maintained at 0°-5° C
  2. additionOn completion of the addition
  3. customthe precipitated solid was collected
  4. customcrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-24bcbf98e3e341d2b6529dc750799a1b
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

Loading…