Process for the preparation of 2,4-dinitrophenyl ethers

• US 4,695,656 A
• Filed: 03/31/1986
• Issued: 09/22/1987
• Est. Priority Date: 04/27/1985
• Status: Expired due to Fees

• Current Assignee: Cassella Aktiengesellschaft (Sanofi )
• Original Assignee: Cassella Aktiengesellschaft (Sanofi )
• Inventors: Schophoff, Friedrich, Reh, Kuno
• Primary Examiner(s): EVANS, JOSEPH
• Application Number:
  US06/846,011
• Time in Patent Office: 540 Days
• Field of Search: 568/711, 568/583, 568/584, 568/586, 568/587, 549/491
• US Class Current: 568/587
• CPC Class Codes: C07C 201/12 by reactions not involving the formation of nitro groups
• CPC Class Codes: C07C 205/37 the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
• CPC Class Codes: C07D 307/12 Radicals substituted by oxygen atoms

Abstract

2,4-Dinitrophenyl ethers are prepared by reacting a 2,4-dinitrochlorobenzene or 2,4-dinitrobromobenzene with an alkali metal alcoholate in a non-polar, inert solvent, at a temperature from -25° C. to 50° C.

Claims

1. In the improved process for the preparation of 2,4-dinitrophenyl ethers of the formula ##STR3## wherein R is (C₁ -C₄)alkoxy-(C₂ -C₄)alkyl, phenoxy-(C₂ -C₄)alkyl, (C₁ -C₄)alkoxy-(C₂ -C₄)alkoxy-(C₂ -C₄)alkyl or tetrahydrofurfuryl, wherein 2,4-dinitrohalobenzene of the formula ##STR4## is reacted with an alkali metal alcoholate of the formula

View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)

2. The process according to claim 1 wherein the molar ratio of 2,4-dinitrohalobenzene:

alkali metal alcoholate is 1;

(1 to 1.2).

3. The process according to claim 1 wherein the reaction temperature is from -5°

to 25°

C.

4. The process according to claim 3 wherein the reaction temperature is from 0°

to 7°

C.

5. The process according to claim 1 wherein a solution of 2,4-dinitrohalobenzene is mixed with a solution or suspension of the alkali metal alcoholate.

6. The process according to claim 1 wherein a solution of the 2,4-dinitrohalobenzene of the formula II is initially introduced into a reaction vessel and then a solution or suspension of the alkali metal alcoholate is added.

7. The process according to claim 1 wherein 2,4-dinitrohalobenzene is 2,4-dinitrochlorobenzene.

8. The process according to claim 1 wherein the alkali metal alcoholate is alkali metal 2-methoxyethanolate.

9. The process according to claim 1 wherein the alkali metal alcoholate is sodium alcoholate.

10. The process according to claim 1 wherein the inert solvent is a solvent which has a dipole moment from 0 to 3.3×

10^-30 Cm.

11. The process according to claim 1 wherein the inert solvent is benzene, toluene, xylene, ethylbenzene, tetralin or mixtures thereof.

12. An improved process for preparation of 2,4-dinitrophenyl ethers which comprises reacting a 2,4-dinitrohalobenzene with 2-methoxy-ethanolate at -25°

to 50°

C. in the presence of a non-polar, inert solvent.