Author Topic: patents: isosafrole halohydrin/epoxide  (Read 1382 times)

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patents: isosafrole halohydrin/epoxide
« on: May 31, 2002, 05:11:00 PM »

Patent JP60048982

, 1985-03-16
PURPOSE: To produce the titled compound useful as an intermediate of synthetic
perfumery and pharmaceuticals, in high yield and selectivity in an industrial scale,
by the electrolysis of isosafrole in a mixture of an organic solvent and an acidic-basic
water containing a halogen compound.
CONSTITUTION: A halogen compound (preferably a bromide such as sodium bromide)
is dissolved preferably in high concentration in a mixture of an acidic or basic water (e.g.
water added with sulfuric acid, sodium hydroxide, etc.) and an organic solvent (e.g.
acetonitrile). The isosafrole halogydrin of formula I (X is halogen) and/or isosafrole epoxide
of formula II can be produced by electrolyzing isosafrole in the above mixture using e.g. a
platinum electrode at an electrical current density of 1-100mA/cm2 at 0-70 deg.C. The
amount of the organic solvent is 5-50 liters per 1mol of isosafrole, and that of water is
1/50-10pts. per 1pt. of the organic solvent.

Patent GB746042

, 1956-03-07
"improvements in the production of styrene halohydrins and homologues thereof"
abstract: Halohydrins of styrene and its homologues are made by reacting styrene or a
homologue thereof with an aqueous solution containing halogen ions and hydrogen ions
in the presence of a water-soluble oxidizing agent. A preferred oxidizing agent is
hydrogen peroxide, but organic peroxides, permanganates, chromium trioxide,
bichromates, peracetic acid, chloric acid and perchloric acid also are referred to.
Aqueous solutions of hydrohalic acids are suitable sources of hydrogen and halogen
ions. In examples (1) hydrogen peroxide is added to an aqueous solution of hydrochloric
acid and styrene to give styrene chlorohydrin; (2) styrene is treated with hydrobromic
acid, sulphuric acid and potassium permanganate to give styrene bromohydrin; (3)
styrene is similarly treated with hydrobromic acid and peracetic acid; (4) styrene is
treated with hydrobromic acid and hydrogen peroxide; (5) styrene is treated with
aqueous sodium bromide, sulphuric acid and hydrogen peroxide to give styrene
bromohydrin, which may then be reduced to phenylethyl alcohol by the process of
Specification 699,062; (6) styrene is treated with water and bromine, more styrene is
added, followed by hydrogen peroxide; and (7) 4-methylstyrene is treated with
hydrobromic acid and hydrogen peroxide to yield 4-methylstyrene bromohydrin,
which may then be reduced as in Specification 699,062 to 4 - methylphenylethanol.
Specification 746,043 also is referred to.

"Whatever there is to learn has to be learned the hard way."
Castaneda's teacher Don Juan Matus


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W/ bleach?
« Reply #1 on: June 06, 2002, 05:12:00 AM »
I seem to remember there being a discussion of adding bleach to an acidic solution of an olefin to produce halohydrins...  What that debunked?  Or is it valid?