Water → 8-Methoxy-3,7-dimethyl-octa-1,6-dien-3-ol
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
Product 1
Reagents, catalysts & solvents 1
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.