Water → Propan-2-yl (3-hydroxyphenyl)carbamate

HRID 2308964Notes

Reaction equation

HRID 2308964 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[O-2].[Mg+2].O.Cl[C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14]>C(OCC)(=O)C>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][C:13](=[O:14])[O:15][CH:16]([CH3:18])[CH3:17])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7917Isopropyl chloroformateHCID 115683-AminophenolHCID 6850729Magnesium monoxide

Product 1

HCID 15566852Propan-2-yl (3-hydroxyphenyl)carbamateYield 83.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-aminophenol (109 g), magnesium oxide (25 g), water (350 ml) and ethyl acetate (100 ml) was stirred vigorously at room temperature while isopropyl chloroformate (123 g) was added slowly. An ice bath was employed to ensure that the temperature did not exceed 30° C. After stirring for one hour at room temperature, the mixture was filtered to remove insoluble particles. These were washed thoroughly with ether, then the filtrates were combined, then separated, and the organic layers were dried over magnesium sulphate. Evaporation under reduced pressure gave a viscous, pale yellow oil which was crystallised from toluene to give 162.7 g of desired product, mp 75°-77° C.

Workup

  1. additionwas added slowly
  2. customAn ice bath was employed
  3. customdid not exceed 30° C
  4. filtrationthe mixture was filtered
  5. customto remove insoluble particles
  6. washThese were washed thoroughly with ether
  7. customseparated
  8. dry with materialthe organic layers were dried over magnesium sulphate
  9. customEvaporation under reduced pressure
  10. customgave a viscous, pale yellow oil which
  11. customwas crystallised from toluene

Sources & evidence

ORD record
ord-fdc7c0dd988c449da0ecbd689a46007a
Source dataset
uspto-grants-1987_09
Patent number
US04692457

Reaction notes

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