2,4-Dichlorobenzaldehyde → 1-(2,4-Dichlorophenyl)prop-2-en-1-ol

HRID 561508Notes

Reaction equation

HRID 561508 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:11]([Mg]Br)=[CH2:12].[Cl-].[NH4+]>C(OCC)C.O1CCCC1.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH:11]=[CH2:12]

Participants

7

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 202826161-(2,4-Dichlorophenyl)prop-2-en-1-ol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20.0 g (114 mmol) of 2,4-dichlorobenzaldehyde in 200 ml of diethyl ether was slowly added dropwise to 137 ml (137 mmol) of a 1N solution of vinylmagnesium bromide in tetrahydrofuran at RT under argon. After heating under reflux for 1 h, the reaction mixture was added to saturated aqueous ammonium chloride solution and diluted with diethyl ether and water. The phases were separated, and the organic phase was washed twice with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5/1) to result in 18.8 g (81% of theory) of the title compound.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 h
  3. customThe phases were separated
  4. washthe organic phase was washed twice with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-10963d6d95e449428e89e39d7cf88ce4
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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