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

HRID 1171609Notes

Reaction equation

HRID 1171609 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].[Cl-].[NH4+]>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

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 679903-(Trifluoromethyl)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-trifluoromethylbenzaldehyde (6.7 mL) in tetrahydrofuran (40 mL) was stirred on an ice bath and treated dropwise over 25 min with a solution of vinylmagnesium bromide in tetrahydrofuran (1.0 M, 60 mL). The mixture was stirred for 2 h while allowing to warm slowly to room temperature, then was treated with saturated aqueous ammonium chloride. The mixture was extracted with ether, and the organic extracts were washed with water and brine, then dried over sodium sulfate and concentrated under vacuum. Purification by flash column chromatography, eluting with 10% ethyl acetate in hexane, provided 1-(3-trifluoromethylphenyl)prop-2-en-1-ol (2.33 g) as a colorless oil. MS found: (M+H−H2O)+=185.19.

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe organic extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customPurification by flash column chromatography
  6. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2f10b8df439c4d41ac7ff32377a650ce
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

Loading…