4-Aminophenol → ethyl N-(4-hydroxyphenyl)carbamate

HRID 2230250Notes

Reaction equation

HRID 2230250 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>ClCCl>[CH2:19]([O:18][C:16]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 1049PyridineHCID 10928Ethyl chloroformate

Product 1

HCID 602288ethyl N-(4-hydroxyphenyl)carbamateYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g of 4-aminophenol (Mw=109.13; 0.18324 mol) are suspended in 200 cm3 of anhydrous dichloromethane, under an inert atmosphere. The suspension is cooled to a temperature of 0° C. in a bath of ice and 16.4 cm3 of anhydrous pyridine (Mw=79.10; d=0.981; 0.2034 mol) are then added. 17.6 cm3 of ethyl chloroformate (Mw=108.53; d=1.13; 0.18324 mol) are then added dropwise so as to keep the mixture at a temperature below 10° C. The reaction mixture is kept stirring for two hours. The mixture is poured onto one litre of ice-cold water and then extracted with ethyl acetate. The organic phase is washed with water and then dried, filtered and evaporated under vacuum. After recrystallization from a heptane/ethyl acetate mixture, 21 g of a white powder are obtained, which corresponds to a yield of 63%. The melting point of the product obtained is 127.2° C. The 1H NMR spectrum and the elemental analysis are in accordance with the expected product.

Workup

  1. additionare then added
  2. customat a temperature below 10° C
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customAfter recrystallization from a heptane/ethyl acetate mixture, 21 g of a white powder
  9. customare obtained
  10. customThe melting point of the product obtained
  11. customis 127.2° C

Sources & evidence

ORD record
ord-a0e8deff1dd34a2c87c6b75545d973ff
Source dataset
uspto-grants-2002_07
Patent number
US06423854B1

Reaction notes

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