Superacid catalyzed preparation of resorcinol from meta-isopropy

Details Superacid catalyzed preparation of resorcinol from meta-isopropy Superacid catalyzed preparation of resorcinol from meta-isopropy

1980-03-14

1982-07-13

Lone, Werren B.

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

Organic compounds

Oxygen containing

568741, 568798, C07C 3708, C07C 3908

Patent

active

043396143

ABSTRACT:
Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as Nafion-H catalyzed cleavage-rearrangement reaction of meta-isopropylphenol hydroperoxide in the form of its protected ether or ester derivatives, including readily cleavable and reusable trimethylsilyl and trifluoromethanesulfonyl derivates. Part of the process is the preparation of needed meta-isopropylphenol in high purity free of other isomers by treating any mixture of isopropylphenol isomers in an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to six carbon atoms and a Lewis acid fluoride or by alkylating (transalkylating) phenol with a propyl alkylating agent in the presence of the aforementioned superacid systems.

REFERENCES:
patent: 3028410 (1962-04-01), Zimmer
patent: 3882093 (1975-05-01), Cavanaugh
patent: 4041090 (1977-08-01), McClove
patent: 4147726 (1979-04-01), Wu
patent: 4207264 (1980-06-01), Anderson
Olah et al., "J. Amer. Chem. Soc." vol. 98:8 Apr. 14, 1976.
Olah et al., "Science, Reprint Series 5" Oct. 1979, vol. 206 pp. 13-20.
Olah "Friedel--Crafts Chemistry" John Wiley & Sons, New York (1973) pp. 367-371.
Stang et al., "Vinyl Cations" Academic Press 1979 p. 330.
McOmie, "Protective Group in Organic/Chemistry" Plenum Press, 1973 Chapter 4.

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