4-Chlorophenol → Chlorphenesin

HRID 327620Notes

Reaction equation

HRID 327620 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]1[O:11][CH:10]1[CH2:12][OH:13]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]([OH:11])[CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 46844-ChlorophenolHCID 11164Glycidol

Product 1

HCID 7697ChlorphenesinYield 67.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 25.7 g (0.2 mole) of 4-chlorophenol, 18.5 g (0.25 mole) of glycidol and 1 ml of pyridine was stirred and heated at 85°-90° C. overnight. The pot residue was partitioned between ethyl ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to give a gum which crystallized when triturated with petroleum ether (boiling point range, 30°-60° C.). The solid was collected by filtration and recrystallized from isopropyl ether to yield 27.2 g (67%) of off-white solid, mp 73°-75° C. (lit1 mp 77° C.).

Workup

  1. temperatureheated at 85°-90° C. overnight
  2. customThe pot residue was partitioned between ethyl ether and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a gum which
  7. customcrystallized when
  8. customtriturated with petroleum ether (boiling point range, 30°-60° C.)
  9. filtrationThe solid was collected by filtration
  10. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-b316bc97f16042ff8b0cef8609f4af86
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

Loading…