Hydrochloric Acid → Benzenepropanol, 3-(trifluoromethyl)-

HRID 2038586Notes

Reaction equation

HRID 2038586 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](O)=[O:12])[CH:6]=[CH:7][CH:8]=1.CSC.B.Cl>O1CCCC1>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Conditions

Temperature
2.5 °C

Procedure

Compound obtained from Example 1 (0.463 moles, 100 gms) was suspended in 500 ml of tetrahydrofuran under stirring. The reaction mass was cooled to 0-5° C. 94% solution of borane dimethyl sulfide solution (0.62 moles, 50 ml) was added drop wise maintaining the temperature of 0-5° C. The reaction mass was stirred at 25-30° C. for about 10 hours. 10% HCl (100 ml) was added drop wise to the reaction mass at 25-30° C. in about 2 hours and then extracted with toluene (2×250 ml). The organic layer was separated and washed with water (5×500 ml). Toluene was removed completely from the organic layer by distillation under vacuum to isolate the title compound as an oil (85 gms, Yield 90%).

Workup

  1. temperaturewise maintaining the temperature of 0-5° C
  2. stirringThe reaction mass was stirred at 25-30° C. for about 10 hours
  3. extractionextracted with toluene (2×250 ml)
  4. customThe organic layer was separated
  5. washwashed with water (5×500 ml)
  6. customToluene was removed completely from the organic layer by distillation under vacuum

Sources & evidence

ORD record
ord-094bd6517a2148698a354c551e32c8b7
Source dataset
uspto-grants-2013_11
Patent number
US08575393B2

Reaction notes

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