Process for selective C-alkylation of phenols

Details Process for selective C-alkylation of phenols Process for selective C-alkylation of phenols

1985-03-19

1986-06-10

Lone, Werren B.

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

Organic compounds

Oxygen containing

560 61, 560 67, 560109, 560144, 568650, 568706, 568737, 568744, 568766, 568780, C07C 3714, C07C 3906

Patent

active

045944601

ABSTRACT:
Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.

REFERENCES:
patent: 3518318 (1970-06-01), Smutny
patent: 4163864 (1979-08-01), Morita et al.
patent: 4168271 (1979-09-01), Cardenes et al.
patent: 4400545 (1983-08-01), Willis et al.
Dewhirst et al., "J. Org. Chem." vol. 28, pp. 298-802, (1963).
Bader et al., "J. Amer. Chem. Soc." vol. 80, pp. 3073-3076 (1958).
Bolzonia et al., "Angew. Chem. Int. ed vol. 17(9) p. 684 (1978).
Ahluwala et al., "Tetrahedron" vol. 17, p. 1437 (1981).
Smutny, "Annals New York Academy of Science" pp. 125 and 126 (1973).

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