4-Chlorophenol → Chlorphenesin

HRID 1493951Notes

Reaction equation

HRID 1493951 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%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 25.7 g (3.2 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-439f9455b514409c86500617b18c089b
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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