Water → 4,8-Dimethyl-deca-1,6-dien-3-ol

HRID 1414461Notes

Reaction equation

HRID 1414461 reaction equation
[CH3:1][CH:2]([CH2:5][CH:6]=[CH:7][CH:8]([CH3:11])[CH2:9][CH3:10])[CH:3]=[O:4].[CH:12]([Mg]Cl)=[CH2:13].O>O1CCCC1>[CH3:1][CH:2]([CH2:5][CH:6]=[CH:7][CH:8]([CH3:11])[CH2:9][CH3:10])[CH:3]([OH:4])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 962WaterHCID 538397432,6-Dimethyl-oct-4-en-1-alHCID 178461836HCID 178461836, compound

Product 1

HCID 542471304,8-Dimethyl-deca-1,6-dien-3-olYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

54 g (0.35 mole) of 2,6-dimethyl-oct-4-en-1-al are added in the course of 15 minutes to a solution of 0.4 mole of vinyl-magnesium chloride in 2 liters of tetrahydrofuran, whilst cooling with ice. After a reaction time of 30 minutes, the mixture is hydrolyzed with 40 ml of water, the organic phase is isolated and the solvent is distilled off. The reaction product is fractionated, giving 60 g of the above allyl alcohol (yield, 94% of theory). B.p. = 48°-52° C at 0.02 mm Hg; nD25 = 1.4591.

Workup

  1. temperaturewhilst cooling with ice
  2. customAfter a reaction time of 30 minutes
  3. customthe organic phase is isolated
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-dc95a4cd33f74c54bc31df8af529958e
Source dataset
uspto-grants-1977_01
Patent number
US04001336

Reaction notes

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