Cyclohexadiene derivatives and process for preparing the same

Details Cyclohexadiene derivatives and process for preparing the same Cyclohexadiene derivatives and process for preparing the same

1982-06-22

1984-01-31

Reamer, James H.

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

Organic compounds

Oxygen containing

568591, 568361, 204 59R, C07C 49603

Patent

active

044291647

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to novel cyclohexadiene derivatives and to a process for preparing the derivatives.


DISCLOSURE OF INVENTION

The cyclohexadiene derivatives of this invention are novel compounds which have not been disclosed heretofore in literature and which are represented by the formula (I) ##STR4## (wherein --X-- represents ##STR5## --Y-- represents ##STR6## and R.sup.1 and R.sup.2 represent a lower alkyl group.)
Examples of the lower alkyl groups represented by R.sup.1 and R.sup.2 in the formula (I) are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.
The cyclohexadiene derivatives of the formula (I) are prepared for example by processes described below.
Among the derivatives of the formula (I), those in which --X-- represents ##STR7## and --Y-- represents ##STR8## [namely those of the formula (Ia)] are prepared by electrolyzing a compound of the formula (II) given below (wherein R.sup.1 and R.sup.2 are as defined above) in the presence of a lower aliphatic alcohol and a neutral supporting electrolyte. ##STR9## (R.sup.1 and R.sup.2 in the above formulae are as defined above.)
The compounds of the formula (II) to be used as the starting material are known and relatively easily available. Useful compounds of the formula (II) include 2,6-dimethoxy-4-methylphenol, 2,6-diethoxy-4-methylphenol, 2,6-diisopropoxy-4-methylphenol, 2,6-dibutoxy-4-methylphenol, etc.
Examples of lower aliphatic alcohols useful in the foregoing electrolytic reaction are methanol, ethanol, isopropyl alcohol, n-butyl alcohol, etc. The amount of the lower aliphatic alcohol is not particularly limited but is suitably variable over a wide range. It is used in an amount of preferably 500 ml to 15 l, and especially preferably about 5 to about 10 l, per mole of the compound of the formula (II). The extra alcohol acts as the solvent.
Examples of useful neutral supporting electrolytes are quarternary ammonium salts such as p-toluenesulfonic acid tetramethylammonium salt, p-toluenesulfonic acid tetraethylammonium salt, p-toluenesulfonic acid tetrabutylammonium salt and like p-toluenesulfonic acid tetraalkylammonium salts, and perchloric acid tetramethylammonium salt, perchloric acid tetrabutylammonium salt and like perchloric acid tetraalkylammonium salts, sodium formate, sodium acetate and like alkali metal salts of aliphatic carboxylic acid, sodium fluoride, potassium fluoride and like alkali metal fluorides, etc. The amount of the neutral supporting electrolyte to be used, although nonlimitative and suitably determinable over a wide range, is preferably about 0.01 to about 1 mole, and especially preferably about 0.1 to 0.5 mole, per mole of the compound of the formula (II). However, it is more preferred to determine the amount of the supporting electrolyte considering the reaction conditions and economy in view of the amount thereof affecting the voltage.
Preferred electrodes useful in the foregoing reaction are those made of titanium, platinum, carbon, lead dioxide, nickel or the like as the anode, and those made of platinum, carbon, titanium, nickel, stainless steel or the like as the cathode.
The required current density which is among the most important conditions is in the range of 1 to 200 mA/cm.sup.2, preferably 5 to 100 mA/cm.sup.2. A higher current density involved results in reduced current efficiency and in an increased amount of by-products. With a lower current density, a lower productivity results. Therefore, it is of greatest importance in electrolysis to determine optimum reaction conditions. The voltage to be applied in the foregoing electrolytic reaction ranges preferably from about 1.5 to about 15 V, more preferably from about 2 to about 5 V, although widely variable depending on the amount of the supporting electrolyte used.
The electrolytic temperature is in the range of preferably -10.degree. to 50.degree. C., more preferably 10.degree. to 30.degree. C.
With this invention, while the electrolytic reaction can be performed by using a diaphragm, electrolysis involving no

REFERENCES:
patent: 2908692 (1959-10-01), Richard
patent: 4119574 (1978-10-01), Light et al.
patent: 4201639 (1980-05-01), Light et al.
patent: 4250117 (1981-02-01), Takahashi

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