Water → 8-Methoxy-3,7-dimethylocta-1,6-dien-3-ol

HRID 437497Notes

Reaction equation

HRID 437497 reaction equation
[CH3:1][O:2][CH:3](C)[C:4]([CH3:11])=[CH:5][CH2:6][CH2:7][C:8](=[O:10])[CH3:9].[CH:13]([Mg]Cl)=[CH2:14].O>O1CCCC1>[CH3:1][O:2][CH2:3][C:4]([CH3:11])=[CH:5][CH2:6][CH2:7][C:8]([CH3:9])([OH:10])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 962WaterHCID 53786798HCID 53786798, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 539177528-Methoxy-3,7-dimethylocta-1,6-dien-3-olYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

141 g (0.9 mole) of 7-methoxy-6-methyl-oct-5-en-2-one are added to 1 mole of a 1.5 normal solution of vinyl-magnesium chloride in tetrahydrofuran, at below 20° C, in the course of one hour. After a further 2 hours' reaction, hydrolysis is carried out with 100 ml of water, whilst cooling with ice. After a homogeneous salt suspension has formed, the salt and the tetrahydrofuran solution are separated by filtering or centrifuging. The tetrahydrofuran is distilled off under reduced pressure and the reaction product which remains is purified by fractional distillation. 164 g of 8-methoxy-3,7-dimethyl-octa-1,6-dien-3-ol (yield 85%) are obtained. Boiling point 73°-75° C/0.01 bar; nD25 = 1.4676.

Workup

  1. customAfter a further 2 hours' reaction, hydrolysis
  2. temperaturewhilst cooling with ice
  3. customAfter a homogeneous salt suspension has formed
  4. customthe salt and the tetrahydrofuran solution are separated
  5. filtrationby filtering
  6. distillationThe tetrahydrofuran is distilled off under reduced pressure
  7. distillationthe reaction product which remains is purified by fractional distillation

Sources & evidence

ORD record
ord-6664a19cec2f4dc6a0695b347a1f976c
Source dataset
uspto-grants-1977_06
Patent number
US04031141

Reaction notes

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