3,7-Dimethyloct-6-en-1-yl carbonochloridate → HCID 22765455, compound

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Reaction Steps

To a solution of 20.78 g (0.095 mole) of citronellyl chloroformate in 150 ml of tetrahydrofuran was added under a nitrogen atmosphere with cooling and stirring an aliquot (215 ml, 0.101 mole) of the solution of potassium isopropenolate described in EXAMPLE XVIII. The reaction temperature did not rise above 10° C. during addition. After addition was complete the cooling bath was removed and the mixture was poured into 400 ml of diethyl ether, and washed successively with one 300-ml portion and three 400-ml portions of water. The ether layer was separated and dried over magnesium sulfate. Removal of solvent under reduced pressure left a red, slightly viscous residue weighing 20.83 g, which on distillation through a rotary thin-film molecular still at 75° C. skin temperature and 0.10-0.13 mm pressure yielded 12.97 g (56.8%) of citronellyl isopropenyl carbonate as a colorless liquid. The identity of the compound was confirmed by spectral data.

Provenance & Evidence