US4593125A
Expired / Lapsed
US
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Acylation of naphthalenes
Assignee: CNA Holdings LLC
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Filing: 1985-03-13
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Granted: 1986-06-03
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Expires: 2005-03-13
Abstract
Abstract Naphthalene substituted in the 2- or β-position with an electron-donating substituent can be acylated with high regioselectivity in the 6-position by using an acylating agent in substantially anhydrous hydrogen fluoride which functions both as catalyst and solvent.
Inventors
- 👤 Kenneth G. Davenport
- 👤 H. Clay Linstid, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:04
CPC Classifications
C; C07; C07C; C07C35/00; C07C35/22; C07C35/23; C07C49/00; C07C49/76; C07C49/84; C07C323/00; C07C45/00; C07C45/45; C07C45/46; C07C45/61; C07C45/67; C07C45/76; C07C49/782; C07C49/788; C07C49/80; C07C49/813; C07C49/82; C07C49/83
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
79 words
A method for the acylation of a naphthalene compound of the formula: ##STR3## wherein R is an ortho-para directing electron-donating group not reactive with hydrogen fluoride, with an acylating agent which comprises contacting a reaction mixture of the naphthalene compound and the acylating agent with substantially anhydrous hydrogen fluoride at from about 40° to about 100° C. for a time sufficient to cause substantially complete acylation of the naphthalene compound to the 6-acylnaphthalene compound and isolating the product therefrom.
Claim 2
Independent Claim
79 words
A method for the acylation of a naphthalene compound of the formula: ##STR3## wherein R is an ortho-para directing electron-donating group not reactive with hydrogen fluoride, with an acylating agent which comprises contacting a reaction mixture of the naphthalene compound and the acylating agent with substantially anhydrous hydrogen fluoride at from about 40° to about 100° C. for a time sufficient to cause substantially complete acylation of the naphthalene compound to the 6-acylnaphthalene compound and isolating the product therefrom.
Claim 3
Dependent Claim
33 words
The method of claim 1 wherein the acylating agent is a member of the group consisting of lower alkyl carboxylic acids, lower alkyl carboxylic acid anhydrides, lower alkyl carboxylic acid halides, and ketene.
Claim 4
Dependent Claim
24 words
The method of claim 1 wherein R is a member of the group consisting of hydroxy, lower alkyl, lower alkoxy, lower alkylthio, and halo.
Claim 5
Dependent Claim
31 words
The method of claim 1 wherein the temperature of acylation is from about 60° to about 80° C. and the time of reaction is from about 30 to about 90 minutes.
Claim 6
Dependent Claim
25 words
The method of claim 1 wherein the naphthalene compound to hydrogen fluoride mole ratio in the reaction mixture is from about 1:25 to about 1:50.
Claim 7
Independent Claim
106 words
A method for the acylation of a naphthalene compound of the formula ##STR4## wherein R is a member of the group consisting of hydroxy, lower alkyl, lower alkoxy, lower alkylthio, and halo with an acylating agent of the group consisting of lower alkyl carboxylic acids, lower alkyl carboxylic acid anhydrides, lower alkyl carboxylic acid halides, and ketene by contacting a reaction mixture of the naphthalene compound and the acylating agent with substantially anhydrous hydrogen fluoride at from about 40 to about 100° C. for a time sufficient to cause substantially complete acylation of the naphthalene compound to the corresponding 6-acylnaphthalene compound and isolating the product therefrom.
Claim 8
Independent Claim
106 words
A method for the acylation of a naphthalene compound of the formula ##STR4## wherein R is a member of the group consisting of hydroxy, lower alkyl, lower alkoxy, lower alkylthio, and halo with an acylating agent of the group consisting of lower alkyl carboxylic acids, lower alkyl carboxylic acid anhydrides, lower alkyl carboxylic acid halides, and ketene by contacting a reaction mixture of the naphthalene compound and the acylating agent with substantially anhydrous hydrogen fluoride at from about 40 to about 100° C. for a time sufficient to cause substantially complete acylation of the naphthalene compound to the corresponding 6-acylnaphthalene compound and isolating the product therefrom.
Claim 9
Dependent Claim
31 words
The method of claim 6 wherein the temperature of acylation is from about 60° to 80° C. and the time of reaction is from about 30 minutes to about 90 minutes.
Claim 10
Dependent Claim
25 words
The method of claim 6 wherein the naphthalene compound to hydrogen fluoride mole ratio in the reaction mixture is from about 1:25 to about 1:50.
Claim 11
Independent Claim
53 words
A method for the manufacture of 6-hydroxy-2-acetylnaphthalene which comprises contacting a reaction mixture of acetic anhydride and 2-naphthol with hydrogen fluoride in a mole ration of 2-naphthol to hydrogen fluoride of 1:50 at from about 60° to about 80° C. for about 30 minutes to about 90 minutes and isolating the product therefrom.
Claim 12
Independent Claim
53 words
A method for the manufacture of 6-hydroxy-2-acetylnaphthalene which comprises contacting a reaction mixture of acetic anhydride and 2-naphthol with hydrogen fluoride in a mole ration of 2-naphthol to hydrogen fluoride of 1:50 at from about 60° to about 80° C. for about 30 minutes to about 90 minutes and isolating the product therefrom.
Claim 13
Dependent Claim
19 words
The method of claim 9 wherein the reaction is carried out at about 80° C. for about 60 minutes.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-06-02 | 1989-12-02 | 1990-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-02 | 1993-12-02 | 1994-06-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-02 | 1997-12-02 | 1998-06-03 | $7700.00 | Window Closed / Lapsed |