Isobutyraldehyde → Benzene, [(2-methyl-1-propenyl)thio]-

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Reaction Steps

To a solution of 3.92 g (20 mmol) of phenylthiomethyltrimethylsilane in 10 ml THF at 0° is added 20 ml n-butyllithium in hexane. The resulting yellow solution is stirred for 15 min at 0°, and a solution of 1.44 g (20 mmol) of 2-methyl-1-propanal in 5 ml THF is added. The reaction mixture is stirred for 15 min at 0°, then for 2 hr at 25°. Brine (15 ml) is added and the product extracted with ether. The organic layer is dried over calcium sulfate, filtered and the solvent is removed under vacuum to give 2-methyl-1-propenyl phenyl sulfide, which is purified by distillation under vacuum.

Provenance & Evidence