Diethyl Ether → 3-[4-(3-Hydroxy-2,2-dimethoxypropoxymethyl)benzylidene]-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

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Reaction Conditions

Reaction Steps

A solution of 3-(4-bromomethylbenzylidene)-4,7,7-trimethylbicyclo[2.2.1]-heptan-2-one (C. Bouillon, C. Vayssie, in Ger. Offen., (Oreal S. A., Fr.). Appl: DE 19780314. 78-2811041, 1978, p. 71. C. Bouillon, C. Vayssie, in Fr. Demande, (Oreal S. A., Fr.), Fr, Number 2421878, 1979, p. 31. C. Bouillon, C. Vayssie, (Oreal S. A., Fr.). Ca, Number 1113480, 1981, p. 61) (10.0 g, 30 mmol) in THF (30 ml) is slowly added dropwise at 40° C. with stirring to a solution of 2,2-dimethoxy-1,3-propanediol (M. W. Chun, D. H. Shin, H. R. Moon, J. Lee, H. Park, L. S. Jeong, Bioorg. Med. Chem. Lett 1997, 7, 1475. E. Cesarotti, P. Antognazza, M. Pallavicini, L. Villa, Helv. Chim. Acta 1993, 76, 2344. E. L. Ferroni, V. DiTella, N. Ghanayem, R. Jeske, C. Jodlowski, et al., J. Org. Chem. 1999, 64, 4943) (8.17 g, 60 mmol) and t-BuOK (4.50 g, 40 mmol) in t-BuOH (150 ml). E is stirred at 40° C. for 30 min and subsequently at the reflux temperature for 1 h. After the reaction mixture has been cooled, diethyl ether (30 ml) and water (100 ml) are added. The organic phase is separated off, and the aqueous phase is extracted with diethyl ether (3×50 ml). The combined organic phases are washed with saturated sodium chloride solution (3×70 ml) and dried over magnesium sulfate; the solvent is removed. Work-up by column chromatography using ethyl acetate:cyclohexane 1:1 gives

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