Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonate esters
Patent
1985-09-16
1987-02-24
Chan, Nicky
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfonate esters
558 51, 558 50, 558 48, 564170, 568812, 568437, 568436, 568426, 568424, 568442, C07C14368, C07C 3322, C07C10322
Patent
active
046458522
ABSTRACT:
In an improved process of converting a 1,2-epoxy-2-phenylbutane or a 1,2-epoxy-2-phenylpentane to a 2-hydroxy-2-phenylbutylsulfonate, sulfamate, or halide, or the corresponding 2-hydroxy-2-phenylpentyl compound, respectively, by the reaction at about 40.degree. to 120.degree. C. in the presence of an organic solvent of the requisite epoxybutane or epoxypentane with a proton source and a nucleophile. The proton source can be a free strong acid such as a sulfonic, sulfamic acid, or hydrohalide acid, or the proton source can be derived from an equilibrium system comprising a free strong acid and weak base in equilibrium with the respective deprotonated strong acid and protonated weak base. The process is carried out in one step with reduction or avoidance of aldehyde formation by rearrangement of the epoxyalkane.
REFERENCES:
patent: 3900509 (1975-08-01), Markley
patent: 3954440 (1976-05-01), Markley
patent: 4211549 (1980-07-01), Markley et al.
Weissberger, Chemistry of Heterocyclic Compounds, vol. 19, Part I, 1964, pp. 382-384.
Krauss Richard C.
McKendry Lennon H.
Chan Nicky
Savitsky Thomas R.
Schilling Edward E.
The Dow Chemical Company
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