3-(Trifluoromethyl)benzaldehyde → 1-(3-(Trifluoromethyl)phenyl)prop-2-en-1-ol

HRID 410144Notes

Reaction equation

HRID 410144 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[CH:13]([Mg]Br)=[CH2:14]>O1CCCC1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[C:5]([CH:6]([OH:7])[CH:13]=[CH2:14])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 210748221-(3-(Trifluoromethyl)phenyl)prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(Trifluoromethyl)benzaldehyde (100 g) was added to a pre-cooled (0 to 5° C.) solution of vinyl magnesium bromide (862 mL; 1M) in tetrahydrofuran under the nitrogen atmosphere. The reaction mixture was stirred at room-temperature for one hour. After completion, the reaction was quenched with de-ionized water (500 mL) and dichloromethane (500 mL) was added. The dichloromethane layer was washed with sodium bicarbonate solution (7%; 500 mL), layers were separated and organic layer was concentrated under vacuum at 40° C. to 45° C. to give 1-[3-(trifluoromethyl)phenyl]prop-2-en-1-ol as oil.

Workup

  1. customAfter completion, the reaction was quenched with de-ionized water (500 mL) and dichloromethane (500 mL)
  2. additionwas added
  3. washThe dichloromethane layer was washed with sodium bicarbonate solution (7%; 500 mL), layers
  4. customwere separated
  5. concentrationorganic layer was concentrated under vacuum at 40° C. to 45° C.

Sources & evidence

ORD record
ord-7ad392e2c6e44a7bbb81d8ad2ef76683
Source dataset
uspto-grants-2014_06
Patent number
US08759586B2

Reaction notes

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