Hydrochloric Acid → Benzyl (4-hydroxyphenyl)carbamate

HRID 1780283Notes

Reaction equation

HRID 1780283 reaction equation
C(=O)([O-])O.[Na+].[CH2:6]([O:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:17]1[C:22]([NH2:23])=[CH:21][CH:20]=[C:19]([OH:24])[CH:18]=1.Cl>O.O1CCOCC1>[CH2:6]([O:13][C:14]([NH:23][C:22]1[CH:17]=[CH:18][C:19]([OH:24])=[CH:20][CH:21]=1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 293061Benzyl (4-hydroxyphenyl)carbamateYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

10.1 g (0.12 mol) of sodium hydrogencarbonate and 17.2 ml (0.12 mol) of benzyloxycarbonyl chloride were added at 0° C. to a suspension of 12.5 g (0.11 mol) of p-aminophenol in 100 ml of a 1:1 by volume mixture of dioxane and water, and the mixture was stirred at room temperature for 18 hours. At the end of this time, the reaction mixture was acidified with 2N aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was triturated with a 1:1 by volume mixture of hexane and diethyl ether, to give 22.8 g of the title compound as colorless crystals, melting at 156°-157° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe residue was triturated with a 1:1 by volume mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-743e0762572c41b68936fb6d51ce2c03
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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