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

HRID 1382372Notes

Reaction equation

HRID 1382372 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 moles (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. additionTo a mixture of 129 g
  2. temperatureThe resulting mixture was heated in a steam bath at 65° C. overnight
  3. extractionextracted with 300 ml
  4. extractionThe ether extract
  5. washwas washed successively with 1N sodium hydroxide, water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe dried ether solution was concentrated
  8. distillationthe oily residue was distilled under reduced pressure
  9. customyielding 152 g

Sources & evidence

ORD record
ord-a053dd483a8a46e894ced496d1d4b312
Source dataset
uspto-grants-1989_02
Patent number
US04806555

Reaction notes

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