Carbon Dioxide → 6-Chloro-7-methylene-3-methyl-1-octen-3-yl acetate

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Reaction Conditions

Reaction Steps

A stirred mixture of linalyl acetate (39 g, 0.2 mol), 65% calcium hypochlorite (22 g, 0.1 mol), water (70 mL) and dichloromethane (700 mL) was cooled to 10° C. and solid carbon dioxide was added until an exotherm was no longer observed upon addition. After stirring for an additional 1 h at 10° C., the organic layer was separated and washed successively with a solution containing 5% sodium bicarbonate and 1% sodium bisulfite (100 mL), and then with brine (100 mL). The organic layer was dried, the solvent evaporated, and the residue distilled to yield 41 g of 3-acetoxy-6-chloro-3,7-dimethyl-1,7-octadiene, bp 75°-80° C. (0.5 mm). IR (film) 1740, 1370, 1250, 920 cm-1. NMR (CDCl3) δ1.53 (3H, s), 1.8 (3H, bs), 1.8-2.4 (2H, m), 4.33 (1H, m), 4.84-5.33 (4H, complex) 6.0 (1H, dd).

Provenance & Evidence