Water → HCID 86734360, compound

HRID 1414459Notes

Reaction equation

HRID 1414459 reaction equation
[CH3:1][CH:2]([CH2:5][CH3:6])[CH:3]=[O:4].[CH:7]([Mg]Cl)=[CH2:8].O>O1CCCC1>[CH3:1][CH:2]([CH2:5][CH3:6])[CH:3]([OH:4])[CH:7]=[CH2:8].[CH2:3]([OH:4])[CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 72842-MethylbutanalHCID 178461836HCID 178461836, compound

Product 1

HCID 86734360HCID 86734360, compoundYield 122.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

215 g (2.5 moles) of 2-methylbutan-1-al are added to a solution of 2.6 moles of vinyl-magnesium chloride in 2 liters of tetrahydrofuran in the course of one hour, whilst cooling with ice. After a reaction time of one hour, the mixture is hydrolyzed with 260 ml of water and the organic phase is isolated. The solvent is distilled off and the reaction product is fractionated, giving 263 g of the allyl alcohol 4-methyl-hex-1-en-3-ol. This corresponds to a yield of 93% of theory, based on 2-methylbutan-1-al employed. B.p. = 75° - 77° C at 50 mm Hg; nD25 = 1.4346.

Workup

  1. temperaturewhilst cooling with ice
  2. customAfter a reaction time of one hour
  3. customthe organic phase is isolated
  4. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-d053db6b5c8d4e639084fe1ca3e26733
Source dataset
uspto-grants-1977_01
Patent number
US04001336

Reaction notes

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