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Method of producing p-hydroxyphenylalkanols

A phenyl, phenoxy technology, applied in the field of preparing p-hydroxyphenyl alkanol, can solve the problems such as satisfactory yield and unsatisfactory reactivity of p-hydroxyphenyl alkanol

Inactive Publication Date: 2007-03-28
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned method has a problem that, under relatively mild conditions, the reactivity is unsatisfactory, but, under relatively severe conditions, the amount of by-product impurities increases, so p-hydroxyphenylalkane Alcohol yields are not always satisfactory

Method used

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  • Method of producing p-hydroxyphenylalkanols
  • Method of producing p-hydroxyphenylalkanols
  • Method of producing p-hydroxyphenylalkanols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0261] Into a pressure vessel were charged 62.4 g (0.38 mol) of 2-methyl-6-butylphenol, 14.7 g (0.76 mol) of 28% sodium methoxide and 17.4 g (0.076 mol) of titanium tetraethoxide in methanol. The mixture was heated under reduced pressure, and a mixture of 13.0 g (0.41 moles) of methanol and 14.1 g (0.31 moles) of ethanol was distilled from the reaction system, and thereafter, 53.2 g (0.92 moles) of allyl alcohol and 38.7 g (0.42 moles) of mol) toluene was added to the reaction system, and the reaction was carried out in a nitrogen atmosphere. Then, the reaction system was tightly closed, heated to 210° C., and kept at this temperature for 7 hours. Then, the reaction system was cooled to room temperature, and the reaction was analyzed by gas chromatography. A sample of the solution was analyzed and the yield of the desired product, 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanol, was 78%.

Embodiment 2

[0263] 5.2 g (0.027 moles) of 28% sodium methoxide in methanol and 10.6 g (0.33 moles) of methanol were added to the reaction vessel, followed by 0.67 g (0.027 moles) of magnesium and heating was carried out under a nitrogen atmosphere to Methanol started to flow countercurrently, and 0.06 g (0.027 mol) of hydrogen was removed from the reaction system. After the heating was maintained, the volatilization of hydrogen stopped.

[0264] After the hydrogen volatilization stopped, 45g (0.27 mole) of 2-methyl-6-tert-butylphenol was added to the solution obtained above, the mixture was heated under reduced pressure, and 15g (0.47 mole) was distilled from the reaction system methanol, then add 15.9g (0.27 mole) of allyl alcohol and 13.5g (0.15 mole) of toluene, the solution obtained after adding toluene and allyl alcohol is transferred to a pressure vessel, the atmosphere is nitrogen, and sealed and heated to 210°C and kept at this constant temperature for 4 hours. Then, the reaction...

Embodiment 3

[0266] After adding 23 g (0.14 mol) of 2-methyl-6-tert-butylphenol to reactor A, 14 ml (0.03 mol) of butylmagnesium chloride in diethyl ester were added.

[0267] After adding 23 g (0.14 mol) of 2-methyl-6-tert-butylphenol to another reactor B, 0.62 g (0.03 mol) of sodium was added in a nitrogen atmosphere.

[0268] The solution obtained above in reaction vessels A and B was transferred to a pressure vessel for stirring, then 15.9 g (0.27 moles) of allyl alcohol was added, the atmosphere of the reaction vessel was nitrogen, sealed and heated to 210 ° C, maintained The same temperature was cooled to room temperature for 4 hours, and the sample was analyzed by gas chromatography, and the productive rate of the product 3-(3-tert-butyl-4-hydroxyl-5-methylphenyl) propanol to be obtained was 80%.

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Abstract

Disclosed is a method of producing a p-hydroxyphenylalkanol of formula (I): <CHEM> wherein R<1> and R<2> independently represent hydrogen, alkyl, phenyl which may be substituted with alkyl, or the like, R<3>, R<4>, R<5>, R<6> and R<7> independently represent hydrogen or alkyl and n denotes an integer from 0 to 7, which method comprises reacting a phenol compound of formula (II): <CHEM> wherein R<1> and R<2> are as defined above, with an unsaturated alcohol of formula (III): R<3>R<4>C=C(R<5>)-C(R<6>)(R<7>)-(CH2)n-OH wherein R<3>, R<4>, R<5>, R<6>, R<7> and n are as defined above, in the presence of (A) at least one member selected from the group consisting of alkali metals, alkali-metal compounds, alkaline earth metals and alkaline earth metal compounds and (B) at least one member selected from the group consisting of transition metals and transition metal compounds, or 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.

Description

technical field [0001] This invention relates to a process for the preparation of p-hydroxyphenyl alkanols. Background technique [0002] p-Hydroxyphenylalkanol is a useful compound as a raw material for the production of stabilizers for thermoplastic resins, pharmaceuticals and the like. [0003] As a method for preparing p-hydroxyphenyl alkanols of the following molecular formula: [0004] [0005] Among them, R 11 and R 12 independently represents a hydrogen atom, C 1-8 Alkyl, C 5-8 Cycloalkyl, C 6-12 Alkylcycloalkyl, can be C 1-8 Alkyl substituted C 7-12 Aralkyl, can be replaced by a C 1-8 Alkyl substituted phenyl, can be replaced by a C 1-8 Alkyl-substituted phenoxy, R 13 and R 14 independently represents a hydrogen atom or a C 1-8 the alkyl group, and [0006] n represents an integer of 0-7, and a method is known in which phenol is represented by the following formula: [0007] [0008] React with the unsaturated alcohol represented by the following...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/11C07C37/14C07C39/06
CPCC07C37/14C07C39/11C07C29/32
Inventor 村上力
Owner SUMITOMO CHEM CO LTD