Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals and process

Details Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals and process Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals and process

1978-01-26

1979-07-03

Helfin, Bernard

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

Organic compounds

Oxygen containing

260464, 260586R, 568670, 568648, C07C 4100, C07C 4300

Patent

active

041601092

ABSTRACT:
Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals of the formula ##STR1## wherein each R is a primary or secondary C.sub.1-4 alkyl radical are obtained by catalytic hydrogenation of p-benzoquinone tetramethyl-diketal with about 1 mol of H.sub.2 per mole of diketal, in a basic medium, at a temperature of from about -10.degree. to +150.degree. C. and optionally by reketalization with a primary or secondary C.sub.2-4 alcohol in a slightly acid medium with substantial exclusion of water, at a temperature of from about -10.degree. to +35.degree. C. Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals, optionally dissolved in an alcohol ROH give hydroquinone dialkyl ethers on acidification and heating to about 60.degree. to 120.degree. C., which ethers are valuable dyestuff intermediates. On catalytic hydrogenation in a basic medium, cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals give the corresponding cyclohexane-(1,4)-tetraalkyldiketals, which are the starting products for the manufacture, for example, of tetracyanoquinodimethane, an important compound in the field of semiconductors.

REFERENCES:
patent: 3127450 (1964-03-01), Lorette et al.
patent: 3170958 (1965-02-01), Howard
patent: 4082809 (1978-04-01), Pistorius et al.
Howard et al., Jour. of Org. Chem., vol. 26 (1961), pp. 1026-1028.

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