3-Chloro-2-methyl-1-propene → 2,5,5-Trimethylocta-1,6,7-trien-4-ol

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Reaction Conditions

Reaction Steps

300 ml of absolute ether were added to 7.29 g (0.30 mole) of dry Mg, the mixture was cooled to 15±1° C., and 27.19 g (0.30 mole) freshly distilled β-methylallyl chloride were added. The mixture was stirred over night at the same temperature. The white suspension was cooled to 0° C., and 11.03 g (0.10 mole) 1a in 150 ml absolute ether were added dropwise during 1 hour. The mixture was stirred at 0° C. for 4 hours (reaction monitored on GC). 37 ml of saturated NH4Cl solution were added with vigorous stirring. The solution was decanted from the magnesium salts which were washed several times with ether. The combined ether phases were dried (MgSO4). Distillation gave 14.22 g (91%) 2a, b.p. 60°-1° C./1.5 mm Hg.

Provenance & Evidence