Propionyl chloride → 1-Methyl-4-methylene-6-propionyloxy-2,3,3a,4,5,6,7,8-octahydroazulene

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Reaction Steps

A solution of 2.5 g of 6-hydroxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene in 5 ml of pyridine and 50 ml of methylene chloride was treated at -10° with 1.73 ml of propionyl chloride. After 3 hours stirring, the solution was poured on to ice and worked up in a conventional manner. After distillation of the crude produce under high vacuum, there were obtained 3.15 g (96%) of pure 1-methyl-4-methylene-6-propionyloxy-2,3,3a,4,5,6,7,8-octahydroazulene; b.p0.05 65°-70°; IR(film): νmax = 1380, 1730, 1640, 1460, 1440, 1375, 1340, 1270, 1190, 1158, 1080, 1018, 895 cm- 1. The compound has a woody, spicy, balsamic, slightly earthy odour.

Provenance & Evidence