Water → 5724-03-8

HRID 2259436Notes

Reaction equation

HRID 2259436 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.O>O1CCCC1>[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]([OH:11])[CH:1]=[CH2:2])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 680234-FluorobenzaldehydeHCID 178461836HCID 178461836, compound

Product 1

HCID 150949505724-03-8Yield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,550 ml (2.0 mol) of a 1.29 M solution of vinylmagnesium chloride in tetrahydrofuran were introduced into a 4 l stirred flask under nitrogen. Subsequently, while stirring under nitrogen at 30°-35° C., a solution of 222.0 g (1,764 mol) of 4-fluorobenzaldehyde in 2,000 ml of tetrahydrofuran was added over the course of 30 min, cooling the reaction mixture with ice. The mixture was then stirred at room temperature under nitrogen for 2.5 h. Subsequently, while stirring and cooling with ice, 180 ml of water were added, the mixture was filtered with suction, and the residue from the filter was washed 3x with 150 ml of tetrahydrofuran. The filtrates were combined, dried with sodium sulfate and concentrated. 265.7 g (99%) of product were obtained in the form of a yellow-brown oil.

Workup

  1. stirringSubsequently, while stirring under nitrogen at 30°-35° C.
  2. temperaturecooling the reaction mixture with ice
  3. stirringThe mixture was then stirred at room temperature under nitrogen for 2.5 h
  4. stirringSubsequently, while stirring
  5. additionwere added
  6. filtrationthe mixture was filtered with suction
  7. washthe residue from the filter was washed 3x with 150 ml of tetrahydrofuran
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a3d05ef045d442d9a5790a55a87d85b1
Source dataset
uspto-grants-1995_12
Patent number
US05473080

Reaction notes

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