Process for manufacture of resorcinol

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

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568763, C07C 3700, C07C 3707

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052330958

ABSTRACT:
A process for the manufacture of resorcinol is described which relies upon the intermediacy of a .alpha.,.beta.-unsaturated ketone which can be reacted with a hydroxy moiety-containing compound to obtain a resorcinol precursor which is subsequently converted to resorcinol. In a specific embodiment, 2-cyclohexenone is reacted with water to obtain 3-hydroxycyclohexanone which is dehydrogenated to resorcinol. In another embodiment, 2-cyclohexenone is oxidized to cyclohexane-1,3-dione which is dehydragenated obtain resorcinol.

REFERENCES:
patent: 3476808 (1969-11-01), Etherington, Jr. et al.
patent: 3673255 (1972-06-01), Etherington, Jr. et al.
patent: 3692839 (1972-09-01), Wehrli et al.
patent: 3932511 (1976-01-01), Schaafsma et al.
patent: 3950438 (1976-04-01), Schaafsma et al.
patent: 3965187 (1976-06-01), Little et al.
patent: 3987112 (1976-10-01), Lyons
patent: 4018833 (1977-04-01), Muller et al.
patent: 4024196 (1977-05-01), Krekeler et al.
patent: 4072660 (1978-02-01), Muller et al.
patent: 4154762 (1979-05-01), Huang et al.
patent: 4154965 (1979-05-01), Muller et al.
patent: 4160113 (1979-07-01), Meijer et al.
patent: 4192958 (1980-03-01), Hashimoto et al.
patent: 4200553 (1980-04-01), Van Peppen et al.
patent: 4229597 (1980-10-01), Taguchi et al.
patent: 4239921 (1980-12-01), Hasimoto et al.
patent: 4250336 (1981-02-01), Muller et al.
patent: 4273623 (1981-06-01), Hashimoto et al.
patent: 4283567 (1981-08-01), Nambu et al.
patent: 4283570 (1981-08-01), Nakagawa et al.
patent: 4347393 (1982-08-01), Miki
patent: 4377709 (1983-03-01), Muller
patent: 4417076 (1983-11-01), Rozovsky et al.
patent: 4431848 (1984-02-01), Greco
"The Condensed Chemical Dictionary" 8th ed Rev. Hawle, Pub. Renhold N.Y. London SC 1974 pp. 24 and 676.
Smith, H. A. and Stump, B. L., "A Study of the Catalytic Hydrogenation of Hydroxybenzenes Over Platinum and Rhodium Catalysts," J. Amer. Chem. Soc., 1961, vol. 83, pp. 2739-2743.
Yogev, A. and Mazur, Y. "The Keto-Enol Equilibrium in 1,3-Cyclohexanediones," J. Org. Chem., 32, (1967) p. 2162.
Allen, F. "New Resorcinol Plant Benefits From Better Processing Techniques," Chem. Eng. Sep. 25, 1967, pp. 118-120.
Thiessen, R. J., "A New Method for the Preparation of .alpha., .beta.-Unsaturated Carbonyl Compounds," J. Org. Chem., vol. 36, No. 6, (1971).
Chandrasekharan, V., et al., "Synthesis of 5-Alkyl-& 5-Aryl-resorcinols," Indian J. Chem., vol. 16B, (1978), pp. 970-972.
Barton, D. H. R., et al., ".mu.-Oxo-bis(chlorotriphylbismuth):a Mild Reagent for the Oxidation of the Hydroxy Group, Especially in Allylic Alcohols," J.C.S. Chem. Comm. (1978) pp.1099-1100.
Tempesti, E. Montoneri, E., Giuffre, L. and Airoldi, G., "Base-Catalyzed SO.sub.2 -Induced Allylic Oxidation of Cyclohexane with Molecular Oxygen," J. Org. Chem., (1980), 45, pp. 4278-4280.
"A New Preparative Method for 1,3-Dicarbonyl Compounds by the Regioselective Oxidation of .alpha., .beta.-unsaturated Carbonyl Compounds, Catalyzed By PdCl.sub.2 Using Hydroperoxides as the Reoxidant of Pd.sup.0," Chem. Soc. Jap. Chemistry Letters., (1980), pp. 257-260.
"Liquid-Phase Catalytic Hydrogenation of 1,4-Cyclohexanedione: Activity and Selectivity," Med. J. Org. Chem. (1980), 45, pp. 40-43.
Cormier, R., "A Convenient Synthesis of 3,3-dimethylcyclohexane," Synthetic Comm., 11(4) (1981), pp. 295-298.
Matsumoto, M. and Ito, S., "Ruthenium-catalysed Oxidation of Allyl Alcohols by Molecular", J.C.S. Chem. Comm., (1981) pp. 907-908.
Pez, G. P. and Crissey, R. K., "Selective Hydrogenation of Benzene to Cyclohexane With Zirconium Hydride Catalysts," J. Molecular Catalysis, 21, (1983), pp. 393-404.
Tsuji, Y. et al., "Ruthenium-Catalyzed Oxidation of Alcohols and Catechols Using .tau.-Butyl Hydroperoxide," J. Organomet. Chem., 270 (1984), pp. 333-341.
Morrison, R. T. and Boyd, R. N., Organic Chemistry, 32, pp. 964-977.

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