Manufacture of trimethylhydroquinone diacylates

Details Manufacture of trimethylhydroquinone diacylates Manufacture of trimethylhydroquinone diacylates

2006-12-26

2006-12-26

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

07153994

ABSTRACT:
A process for the manufacture of 2,3,5-trimethylhydroquinone diacylate comprising reacting ketoisophorone with an acylating agent in the presence of a NH- or CH-acidic catalyst, particularly certain bis(perfluorinated hydrocarbyl sulphonyl) imides and metal salts thereof and, respectively, certain tris(perfluoroalkanesulphonyl or pentafluorobenzenesulphonyl) methanes and metal salts thereof. The acylating agent is particularly an acid anhydride, an acyl halide or an enol ester. The so-obtained 2,3,5-trimethylhydroquinone diacylate can be converted into (all-rac)-α-tocopherol by transesterification to yield 2,3,5-trimethylhydroquinone and reaction of the latter with isophytol. (all-rac)-α-Tocopherol itself is the most active member of the vitamin E group.

REFERENCES:
patent: T900015 (1972-07-01), Thweatt et al.
patent: 6417409 (2002-07-01), Krill et al.
patent: 2 149 159 (1972-04-01), None
patent: 0 916 642 (1999-05-01), None
patent: 1 028 103 (2000-08-01), None
patent: 1 134 218 (2001-09-01), None
patent: 1 180 517 (2002-02-01), None
patent: WO 98/21197 (1998-05-01), None
Derwent English abstract of DE 2 149 159.

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