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US5087766A
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Process for producing allyl-substituted phenol compound and the product
Assignee: Mitsubishi Chemical Corp
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Filing: 1990-04-20
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Granted: 1992-02-11
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Expires: 2010-04-20
Abstract
Abstract A process for producing an allyl-substituted phenol compound is described, which comprises a combination of a first step in which a phenol is reacted with an allyl halide in the presence of an alkaline aqueous medium to allyl-etherify the phenol and a second step in which the reaction product obtained in the first step and containing the allyl-etherified phenol is subjected to a Claisen rearangement reaction in the absence of a medium. Also, a compound obtained by the above process is described.
Inventors
- 👤 Kaoru Kanayama
- 👤 Shuji Ichikawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 06:33
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C07C37/00; C07C37/01; C07C37/055; C07C39/00; C07C39/12; C07C39/15; C07C41/00; C07C41/01; C07C41/16; C07C43/23
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
93 words
A process for producing an allyl-substituted phenol compound, comprising the steps of: reacting a phenol, in which at least one of the ortho-positions and para-position based on the phenolic hydroxyl group of said phenol is unsubstituted, with an allyl chloride or allyl bromide in the presence of an alkaline aqueous medium at a temperature and for a reaction time sufficient to allyl-etherify said phenol; and then rearranging said allyl-etherified phenol at a temperature and for a time sufficient to rearrange said allyl-etherified phenol by Claisen rearrangement in the absence of a reaction medium.
Claim 2
Dependent Claim
93 words
A process for producing an allyl-substituted phenol compound, comprising the steps of: reacting a phenol, in which at least one of the ortho-positions and para-position based on the phenolic hydroxyl group of said phenol is unsubstituted, with an allyl chloride or allyl bromide in the presence of an alkaline aqueous medium at a temperature and for a reaction time sufficient to allyl-etherify said phenol; and then rearranging said allyl-etherified phenol at a temperature and for a time sufficient to rearrange said allyl-etherified phenol by Claisen rearrangement in the absence of a reaction medium.
Claim 3
Dependent Claim
27 words
A process as claimed in claim 1, wherein the allyl halide is used in an amount of 1.0 to 1.5 equivalent per hydroxyl group of the phenol.
Claim 4
Dependent Claim
18 words
A process as claimed in claim 1, wherein the allyl-etherification is carried out at 40° to 100° C.
Claim 5
Dependent Claim
19 words
A process as claimed in claim 1, wherein the Claisen rearrangement is carried out at 150° to 190° C.
Claim 6
Dependent Claim
14 words
A process as claimed in claim 1, wherein the phenol is a poly(hydroxyphenyl) compound.
Claim 7
Dependent Claim
70 words
An allyl-substituted phenol compound obtained by a process comprising a combination of a first step in which a poly(hydroxyphenyl) compound is reacted with an allyl halide in the presence of an alkaline aqueous medium to allyl-etherify the phenol and a second step in which the reaction product obtained in the first step and containing the allyl-etherified phenol is subjected to a Claisen rearrangement reaction in the absence of a medium.
Claim 8
Dependent Claim
70 words
An allyl-substituted phenol compound obtained by a process comprising a combination of a first step in which a poly(hydroxyphenyl) compound is reacted with an allyl halide in the presence of an alkaline aqueous medium to allyl-etherify the phenol and a second step in which the reaction product obtained in the first step and containing the allyl-etherified phenol is subjected to a Claisen rearrangement reaction in the absence of a medium.
Claim 9
Dependent Claim
32 words
An allyl-substituted phenol compound as claimed in claim 6, wherein the poly(hydroxyphenyl) compound is a polyphenol represented by the following formula (II) ##STR6## wherein n is an integer of 1 to 10.
Claim 10
Dependent Claim
90 words
A process for producing an allyl-substituted phenol compound, which comprises a combination of a first step in which a phenol is reacted with an allyl halide in the presence of an alkaline aqueous medium to allyl-etherify the phenol, a second step in which the reaction product obtained in the first step and containing the allyl-etherified phenol is subjected to a Claisen rearrangement reaction in the absence of a medium, and a third step in which the allyl-substituted phenol compound obtained in the second step is reacted with an allyl halide.
Claim 11
Dependent Claim
90 words
A process for producing an allyl-substituted phenol compound, which comprises a combination of a first step in which a phenol is reacted with an allyl halide in the presence of an alkaline aqueous medium to allyl-etherify the phenol, a second step in which the reaction product obtained in the first step and containing the allyl-etherified phenol is subjected to a Claisen rearrangement reaction in the absence of a medium, and a third step in which the allyl-substituted phenol compound obtained in the second step is reacted with an allyl halide.
Claim 12
Dependent Claim
26 words
A process as claimed in claim 8, wherein the third step is carried out in the presence of an alkaline aqueous medium or an organic solvent.
Claim 13
Dependent Claim
48 words
A process for producing an allyl-substituted phenol compound, which comprises reacting a phenol with an allyl halide in the presence of an alkaline aqueous medium to allyl-etherify the phenol, said allyl halide being used in an amount of 1.5 to 2.0 equivalent per hydroxyl group of the phenol.
Claim 14
Dependent Claim
48 words
A process for producing an allyl-substituted phenol compound, which comprises reacting a phenol with an allyl halide in the presence of an alkaline aqueous medium to allyl-etherify the phenol, said allyl halide being used in an amount of 1.5 to 2.0 equivalent per hydroxyl group of the phenol.
Claim 15
Dependent Claim
29 words
A process as claimed in claim 10, wherein the phenol is a polyphenol represented by the following formula (II) ##STR7## wherein n is an integer of 1 to 10.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-02-10 | 1995-08-12 | 1996-02-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-02-10 | 1999-08-12 | 2000-02-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-02-10 | 2003-08-12 | 2004-02-11 | $7700.00 | Window Closed / Lapsed |