Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2003-03-27
2004-04-06
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S763000
Reexamination Certificate
active
06717020
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method of producing p-hydroxyphenylalkanols.
2. Background of the Invention
p-Hydroxyphenylalkanols are useful compounds as raw compounds for producing stabilizers for thermoplastic resins, raw compounds of pharmaceuticals and the like.
As a method of producing p-hydroxyphenylalkanols of the following formula:
wherein R
11
and R
12
independently represent a hydrogen atom, an C1-8 alkyl group, a C5-8 cycloalkyl group, an C6-12 alkylcycloalkyl group, an C7-12 aralkyl group which may be substituted with an C1-8 alkyl group, a phenyl group which may be substituted with a C1-8 alkyl group, R
13
and R
14
independently represent a hydrogen atom or an C1-8 alkyl group, and
n denotes an integer from 0 to 7, a method is known in which phenols represented by the following formula:
wherein R
11
and R
12
respectively represent the aforementioned meaning, are reacted with unsaturated alcohols represented by the following formula:
CH
2
═C(R
13
)—CH(R
14
)—(CH
2
)
n
—OH
wherein R
13
, R
14
and n respectively represent the same meaning as above, in the presence of a base (Japanese Patent Application Laid-Open (JP-A) No. 2001-64220). The aforementioned method, however, has a problem in that the reactivity is not satisfactory under a relatively mild reaction condition whereas the amount of by-produced impurities increases under a relatively severe condition, hence the yield of p-hydroxyphenylalkanols is not always satisfactory.
SUMMARY OF THE INVENTION
According to the present invention, p-hydroxyphenylalkanols of the following formula (I) can be produced in a good yield.
The present invention provides: as the first aspect of the invention,
1. a method for producing a p-hydroxyphenylalkanol of formula (I):
wherein R
1
and R
2
independently represent
a hydrogen atom,
an C1-8 alkyl group,
an C1-8 alkoxy group,
a C5-8 cycloalkyl group,
an C6-12 alkylcycloalkyl group,
an C7-12 aralkyl group which may be substituted with an C1-8 alkyl group,
a phenyl group which may be substituted with a C1-8 alkyl group,
a phenoxy group which may be substituted with a C1-8 alkyl group,
R
3
, R
4
, R
5
, R
6
and R
7
independently represent a hydrogen atom or an C1-8 alkyl group, and
n denotes an integer from 0 to 7, which method comprises reacting a phenol compound of formula (II):
wherein R
1
and R
2
respectively represent the same as defined above, with an unsaturated alcohol of formula (III):
R
3
R
4
C═C(R
5
)—C(R
6
)(R
7
)—(CH
2
)
n
—OH (III)
wherein R
3
, R
4
, R
5
, R
6
, R
7
and n respectively represent the same as defined, in the presence of
(A) at least one compound selected from the group consisting of an alkali metal, an alkali metal compound, an alkaline earth metal and an alkaline earth metal compound, and
(B) at least one compound selected from the group consisting of a transition metal and a transition metal compound; and
as the second aspect of the invention,
2. a method for producing a p-hydroxyphenylalkanol of formula (I) as defined above, which method comprises reacting the phenol compound of formula (II) as defined above with the unsaturated alcohol of formula (III) as defined above, in the presence of
(a) an alkali metal or an alkali metal compound, and
(b) an alkaline earth metal or an alkaline earth metal compound.
DETAILED DESCRIPTION OF THE INVENTION
A description will be made to the first aspect of the invention.
Examples of the C1-8 alkyl group represented by R
1
or R
2
include, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl, t-pentyl, n-hexyl, n-heptyl, i-octyl, t-octyl and 2-ethylhexyl groups.
Examples of the C1-8 alkoxy group represented by R
1
or R
2
include, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butyloxy, i-butyloxy, sec-butyloxy, t-butyloxy, t-pentyloxy, n-hexyloxy, n-heptyloxy, i-octyloxy, t-octyloxy and 2-ethylhexyloxy groups.
Examples of the C5-8 cycloalkyl group by R
1
or R
2
include, for example, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl groups.
Examples of the C6-12 alkylcycloalkyl group represented by R
1
or R
2
include, for example, 1-methylcyclopentyl, 1-methylcyclohexyl and 1-methyl-4-i-propylcyclohexyl groups.
Examples of the C7-12 aralkyl group which may be substituted with a C1-8 alkyl group represented by R
1
or R
2
include, for example, benzyl, phenylethyl, &agr;-methylbenzyl and &agr;, &agr;-dimethylbenzyl.
Examples of the phenyl group which may be substituted with the C1-8 alkyl group represented by R
1
or R
2
include, for example, a phenyl group, methylphenyl, ethylphenyl, n-propylphenyl, i-propylphenyl, n-butylphenyl, i-butylphenyl, sec-butylphenyl, t-butylphenyl, t-pentylphenyl, n-hexylphenyl, n-heptylphenyl, i-octylphenyl, t-octylphenyl and 2-ethylhexylphenyl groups.
Examples of the phenoxy group which may be substituted with the C1-8 alkyl group represented by R
1
or R
2
include, for example, a phenoxy group, methylphenoxy, ethylphenoxy, n-propylphenoxy, i-propylphenoxy, n-butylphenoxy, i-butylphenoxy, sec-butylphenoxy, t-butylphenoxy, t-pentylphenoxy, n-hexylphenoxy, n-heptylphenoxy, i-octylphenoxy, t-octylphenoxy and 2-ethylhexylphenoxy, 2,6-di-t-butylphenoxy, 2,4-dimethyl-6-t-butylphenoxy groups.
At least one of R
1
and R
2
is preferably the C1-8 alkyl, C1-8 alkoxy, or C5-8 cycloalkyl group, the phenyl group which may be substituted with a C1-8 alkyl group, or the phenoxy group which may be substituted with a C1-8 alkyl group, more preferably an C1-8 alkyl group or a C5-8 cycloalkyl group and particularly preferably a methyl group or a t-alkyl group such as t-butyl, t-pentyl or t-octyl.
Examples of the phenol compound (II) include, for example, phenol, 2-methylphenol, 2-methoxyphenol, 2-t-butylphenol, 2-t-butoxyphenol, 2-t-pentylphenol, 2-t-pentyloxyphenol, 2-octylphenol, 2-cyclohexylphenol, 2-(1-methylcyclohexyl)phenol, 2,6-dimethylphenol, 2,6-dimethoxyphenol, 2-t-butyl-6-methylphenol, 2-t-butoxy-6-methylphenol, 2-t-butyl-6-methoxyphenol, 2-t-pentyl-6-methylphenol, 2-t-octyl-6-methylphenol, 2-cyclohexyl-6-methylphenol, 2-di-t-butoxyphenol, 2-(1-methylcyclohexyl)-6-methylphenol, 2-t-butyl-6-ethylphenol, 2-t-butyl-6-ethoxyphenol, 2-t-pentyl-6-ethylphenol, 2-t-octyl-6-ethylphenol, 2-cyclohexyl-6-ethylphenol, 2-(1-methylcyclohexyl)-6-ethylphenol, 2,6-di-t-butylphenol, 2-t-pentyl-6-t-butylphenol, 2,6-di-t-pentylphenol, 2-t-octyl-6-butylphenol, 2-cyclohexyl-6-t-butylphenol, 2-(1-methylcyclohexyl)-6-t-butylphenol, 2-phenyl-6-methylphenol, 2-phenyl-6-t-butylphenol, 2-tolyl-6-methylphenol, 2-tolyl-6-t-butylphenol, 2,6-diphenylphenol, 2-phenoxyphenol, 2-(2-methylphenoxy)phenol, 2-phenoxy-6-methylphenol, 2-phenoxy-6-t-butylphenol, 2-phenoxy-6-methoxyphenol, 2,6-diphenoxyphenol, 2-(2-methyl-6-t-butylphenoxy)phenol, 2-(2,4-dimethyl-6-t-butylphenoxy)phenol, 2-(2-methyl-6-t-butylphenoxy)-6-methylphenol, and 2-(2,4-dimethyl-6-t-butylphenoxy)-6-methylphenol.
Among these phenol compounds, 2-methyl-6-t-butylphenol or 2,6-di-t-butylphenol is preferably used.
Examples of the C1-8 alkyl group represented by R
3
, R
4
, R
5
, R
6
or R
7
in the unsaturated alcohol of formula (III) include, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl, t-pentyl, n-hexyl, n-heptyl, i-octyl, t-octy, 2-ethylhexyl and the like. R
3
and R
4
are preferably hydrogen atoms.
Examples of the unsaturated alcohol (III) include, for example, allyl alcohol, 2-butene-1-ol, 3-butene-1-ol, 3-butene-2-ol, 2-methyl-2-propene-1-ol, 2-methyl-3-butene-1-ol, 3-methyl-2-butene-1-ol, 2-methyl-3-butene-2-ol, 3-methyl-3-butene-1-ol, 4-pentene-1-ol, 4-penetene-2-ol, 1-pentene-3-ol, 1-hexene-3-ol, 5-hexene-1-ol, 6-heptene-1-ol, 7-octene-1-ol, 8-nonene-1-ol or 9-decene-1-ol. Among these compounds, allyl alcohol is preferably used.
The amount of the unsaturated alcohol (III) that may be suitably used is usually about 0.1 to 10 moles and preferably about 1 to 5 moles per mol of the phenol compound (II).
Examples of the alkali metal include lithium, sodium and potassium.
Examples of the
Shippen Michael L.
Sumitomo Chemical Company Limited
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