3-(Trifluoromethyl)phenol → 2-Butanol, 4-chloro-1-[3-(trifluoromethyl)phenoxy]-

HRID 1639057Notes

Reaction equation

HRID 1639057 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[OH-].[K+].Cl[CH2:15][CH:16]([OH:20])[CH2:17][CH2:18][Cl:19]>O.C(O)(C)C>[Cl:19][CH2:18][CH2:17][CH:16]([OH:20])[CH2:15][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1

Participants

6

Conditions

Temperature
65 °C

Procedure

To a mixture of 0.5 mole (75 g) of m-trifluoromethylphenol, 1 mole (56 g) of potassium hydroxide, 100 ml of water and 400 ml of isopropanol was added 0.6 mole (84 g) of 1,4-dichloro-2-butanol with stirring at temperature below 55° C. The resulting reaction mixture was heated at 65° C. for 20 hr, mixed with 2 liters of water, and extracted with 400 ml of isopropyl ether. The ether extract was washed with 0.5 N sodium hydroxide and then with water, dried over sodium sulfate and distilled under reduced pressure. The distillate which was collected at 120°-124° C./0.01 mm solidified at room temperature and melted at 50°-52° C.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with 400 ml of isopropyl ether
  3. extractionThe ether extract
  4. washwas washed with 0.5 N sodium hydroxide
  5. dry with materialwith water, dried over sodium sulfate
  6. distillationdistilled under reduced pressure
  7. distillationThe distillate which was collected at 120°-124° C./0.01 mm
  8. customsolidified at room temperature

Sources & evidence

ORD record
ord-9e4f49efb4c84a2ba8fc5662ce89bede
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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