Acylation of naphthalenes
AssigneeCelanese Corporation
InventorsKenneth G. Davenport, H. Clay Linstid, III
Life of this patent
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Abstract
Naphthalene substituted in the 2- or .beta.-position with an electron-donating substituent can be acylated with high regioselectivity in the 6-position by using an acylating agent in substantially anhydrous hydrogen fluoride which functions both as catalyst and solvent.
Claims10
A method for the acylation of a naphthalene compound of the formula:
- ##STR3## wherein R is an ortho-para directing electron-donating group not reactive with hydrogen fluoride, with an acylating agent which comprises contacting a reaction mixture of the naphthalene compound and the acylating agent with substantially anhydrous hydrogen fluoride at from about 40.degree. to about 100.degree. C. for a time sufficient to cause substantially complete acylation of the naphthalene compound to the 6-acylnaphthalene compound and isolating the product therefrom.
A method for the acylation of a naphthalene compound of the formula ##STR4## wherein R is a member of the group consisting of hydroxy, lower alkyl, lower alkoxy, lower alkylthio, and halo with an acylating agent of the group consisting of lower alkyl carboxylic acids, lower alkyl carboxylic acid anhydrides, lower alkyl carboxylic acid halides, and ketene by contacting a reaction mixture of the naphthalene compound and the acylating agent with substantially anhydrous hydrogen fluoride at from about 40 to about 100.degree. C. for a time sufficient to cause substantially complete acylation of the naphthalene compound to the corresponding 6-acylnaphthalene compound and isolating the product therefrom.
A method for the manufacture of 6-hydroxy-2-acetylnaphthalene which comprises contacting a reaction mixture of acetic anhydride and 2-naphthol with hydrogen fluoride in a mole ration of 2-naphthol to hydrogen fluoride of 1:50 at from about 60.degree. to about 80.degree. C. for about 30 minutes to about 90 minutes and isolating the product therefrom.
Dependencies are inferred from the claim text.