Water → 4-Chloro-1-(2-chlorophenoxy)-2-butanol

HRID 1639052Notes

Reaction equation

HRID 1639052 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[K+].O.Cl[CH2:13][CH:14]([OH:18])[CH2:15][CH2:16][Cl:17]>C(O)(C)C>[Cl:17][CH2:16][CH2:15][CH:14]([OH:18])[CH2:13][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

6

Conditions

Temperature
50 °C

Procedure

To a mixture of 129 g (1 mole) of 2-chlorophenol, 60 g of potassium hydroxide, 100 ml of water and 400 ml of isopropanol was added 1.3 mole (185.9 g) of 1,4-dichloro-2-butanol with stirring at 50° C. The resulting mixture was heated in a steam bath at 65° C. overnight and extracted with 300 ml of isopropyl ether. The ether extract was washed successively with 1N sodium hydroxide, water and dried over sodium sulfate. The dried ether solution was concentrated and the oily residue was distilled under reduced pressure yielding 152 g of an oily substance (b.p. 130°-131° C./0.01 mm).

Workup

  1. temperatureThe resulting mixture was heated in a steam bath at 65° C. overnight
  2. extractionextracted with 300 ml of isopropyl ether
  3. extractionThe ether extract
  4. washwas washed successively with 1N sodium hydroxide, water
  5. dry with materialdried over sodium sulfate
  6. concentrationThe dried ether solution was concentrated
  7. distillationthe oily residue was distilled under reduced pressure
  8. customyielding 152 g of an oily substance (b.p. 130°-131° C./0.01 mm)

Sources & evidence

ORD record
ord-be417778ba2a4682836b1fbf43a2fe3e
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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