Cycloheptene → 2-[(1-Cyclohepten-3-yl)thio]acetaldehyde

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A solution of 108.13 g (.433 mole) of 3-[2,2-diethoxyethyl)thio]-1-cycloheptene in 1000 ml of acetone/water, 9:1 was treated with 1.1 g of p-toluenesulfonic acid hydrate and heated under reflux for 1.0 hour, cooled, and concentrated. The residue was partitioned between ether/10% sodium bicarbonate. The aqueous phase was further extracted with ether. The organic extracts were pooled, dried over magnesium sulfate, and evaporated to afford 75.30 g (.443 mole, 100%) of 2-[(1-cyclohepten-3-yl)thio]acetaldehyde as a colorless oil.

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