Arotinoic methanol → p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzaldehyde

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Reaction Steps

6.7 g of p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzyl alcohol (prepared as described in Example 12) dissolved in 100 ml of absolute ether are added dropwise within 10 minutes to a stirred suspension, cooled to 0°-5° C., of manganese dioxide in 100 ml of absolute ether. The mixture is stirred at room temperature overnight and then filtered through Celite. The filtrate is concentrated to dryness on a rotary evaporator. The yellowish oil crystallizes. Recrystallisation from ether yields p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzaldehyde in the form of colourless crystals of melting point 140°-141° C.

Provenance & Evidence