Hydrochloric Acid → (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

HRID 1449851Notes

Reaction equation

HRID 1449851 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11]/[CH:12]=[C:13](\[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)/[C:14](OCC)=[O:15].CO.Cl>O>[F:11]/[CH:12]=[C:13](\[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)/[CH2:14][OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 15342053ethyl (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butyrateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10943450(E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cool to 0° C. a solution of diisobutylaluminum hydride (7.64 kg, 25% by weight in toluene, 13.42 mol). Add a solution of ethyl (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butyrate (1.74 kg, 74.1% by weight in toluene, 5.37 mol) at such a rate that the temperature of the reaction mixture does not rise above 20° C. After the addition is complete, warm to ambient temperature. After 2 hours, cool to 0° C. Slowly, add methanol (7.73 kg) at such a rate that the temperature of the reaction mixture does not rise above 15° C. Cool to 0° C. Slowly, add water (7.96 kg) at such a rate that the temperature of the reaction mixture does not rise above 20° C. Add a concentrated aqueous solution of hydrochloric acid (7.59 kg). Warm to ambient temperature. Separate the organic layer and dry azeotropically by distillation in vacuo until the volume of the organic layer is about one half of its original volume to give the title compound as a solution in toluene.

Workup

  1. customdoes not rise above 20° C
  2. additionAfter the addition
  3. temperaturecool to 0° C
  4. customdoes not rise above 15° C
  5. temperatureCool to 0° C
  6. customdoes not rise above 20° C
  7. temperatureWarm to ambient temperature
  8. customSeparate the organic layer
  9. customdry azeotropically by distillation in vacuo until the volume of the organic layer

Sources & evidence

ORD record
ord-c1cfc7202cf649b683e3c9a98977ee4a
Source dataset
uspto-grants-1997_02
Patent number
US05599986

Reaction notes

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