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

HRID 1463127Notes

Reaction equation

HRID 1463127 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 0.5N 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
  3. extractionThe ether extract
  4. washwas washed with 0.5N 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-85bf4917305d45f695dc8f9430971f2e
Source dataset
uspto-grants-1984_07
Patent number
US04463190

Reaction notes

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