Preparation of 6-substituted-2-vinylnaphthalene

C - Chemistry – Metallurgy – 07 – C

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C07C 41/30 (2006.01) C07C 37/11 (2006.01) C07C 39/225 (2006.01) C07C 43/215 (2006.01) C07C 43/285 (2006.01) C07C 45/46 (2006.01) C07C 319/20 (2006.01) C07C 323/09 (2006.01)

Patent

CA 2052185

ATC-0014 CEL-87-116 ABSTRACT A method of forming 6-substituted-2-vinyl naphthalene from a 2-substituted naphthalene compound wherein the substituent in the 2-position is an ortho-para directing electron-donating group not reactive with hydrogen fluoride, comprises contacting the naphthalene compound and an acylating agent with substantially anhydrous hydrogen fluoride to acylate the naphthalene compound to a 6-substituted-2-acylnaphthalene compound, hydrogenating the 6-substituted-2-acylnaphthalene compound to convert the 2-acyl substituent to an alcohol substituent, dehydrating the product of hydrogenation in the presence of a free radical inhibitor to convert the alcohol substituent to an olefinic substituent, and isolating the formed 6-substituted-2-vinylnaphthalene subsequent to the dehydration.

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