Hydrochloric Acid → 1-Cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

The silyl cyanohydrin of Example 3 (40.7 g, 165 mol) was dissolved in 300 ml ethanol and perfused at 0° C. with hydrogen chloride for 30 minutes. After an additional 16 hours at 0° C. the mixture was evaporated in vacuo to an oil. This was taken up in chloroform and washed with 2×100 ml sodium bicarbonate, 1×80 ml water, 1×80 ml brine, dried over magnesium sulfate, filtered, and evaporated in vacuo to a residue which partially crystallized. This solid was triturated with 10% ethereal hexane 17.6 g (62%) mp 55°-59° C. (69°-75° C. after recrystallization from ether/hexane).

Provenance & Evidence