Process for preparing 4-chlorobenzyl propargyl ether

Patent metadata

Field	Value
Publication number	US-11358922-B2
Application number	US-201816756961-A
Country	US
Kind code	B2
Filing date	Oct 31, 2018
Priority date	Nov 2, 2017
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

The present invention relates to a process for preparing 4-chlorobenzyl propargylether comprising a step (a) of reacting 4-chlorobenzyl chloride with propargyl alcohol in the presence of a base and a phase transfer catalyst, wherein the reaction mixture comprises at least two phases, wherein one phase is an organic phase and one phase is an aqueous phase.

First claim

The invention claimed is:

1. A process for preparing a compound of formula I

comprising a step (a) of reacting a compound formula II

with a compound of formula III

in the presence of a base and a phase transfer catalyst in a reaction mixture,
wherein the reaction mixture comprises at least two phases, wherein one phase is an organic phase and one phase is an aqueous phase,
wherein the base is selected from the group consisting of alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal carbonates, alkali metal and alkaline earth metal hydrogen carbonates, alkali metal and alkaline earth metal alcoholates, a tertiary amine, a pyridine, a bicyclic amine, and mixtures thereof, and
wherein the phase transfer catalyst is selected from the group consisting of benzyltrimethylammonioum chloride, tetraethylammonium chloride, tetrapropylammonium bromide, tetrabutylammonium bromide, and tributylmethylammonium chloride,
wherein the process further comprises
(b) adding an organic solvent and/or water to the mixture obtained in the reaction step (a),
(c) separating the at least two phases of the mixture obtained in step (b), and
(f) isolating the compound of formula I from the organic phase obtained in step (c),
wherein the phase separation step (c) comprises the separation of three phases,
wherein one phase is an organic phase, one phase is an aqueous phase, and one phase is a catalyst-containing phase,
wherein the process further comprises isolating the catalyst-containing phase.

2. The process according to claim 1 , wherein the process further comprises
(d) washing the organic phase obtained in step (c) with an aqueous solution.

3. The process according to claim 1 , wherein the process further comprises recycling the catalyst-containing phase for repetition of the process.

4. The process according to claim 1 , wherein the isolation of the compound of formula I in step (f) is performed by subjecting an organic phases to a distillation process.

5. The process according to claim 1 , wherein the phase transfer catalyst is provided in a molar amount of from 0.5 to 20 mol-% based on the molar amount of the compound of formula II.

6. The process according to claim 1 , wherein the base and the compound of formula II are provided in a molar ratio of from 3:1 to 1:1.

7. The process according to claim 1 , wherein the base is selected from the group consisting of alkali carbonates, alkali hydroxides, and mixtures thereof.

8. The process according to claim 7 , wherein the base comprises sodium hydroxide.

9. The process according to claim 1 , wherein the base is sodium hydroxide, which is provided in the form of an aqueous solution.

10. The process according to claim 1 , wherein the organic phase comprises an organic solvent selected from the group consisting of alkanes, aromatic solvents, ethers, and mixtures thereof.

11. The process according to claim 1 , wherein the compound of formula Ill and the compound of formula II are provided in a molar ratio of from 2:1 to 1:1.

12. The process according to claim 11 , wherein the compound of formula Ill and the compound of formula II are provided in the molar ratio of 1.5:1 to 1:1.

13. The process according to claim 1 , wherein the reaction step (a) is performed by providing a mixture comprising the compound of formula II and the phase transfer catalyst in an organic solvent, and adding the compound of formula III simultaneously with an aqueous solution of the base.

14. The process according to claim 13 , wherein the dosing time for adding the compound of formula Ill simultaneously with the aqueous solution of the base is from 0.5 to 3 hours.

15. The process according to claim 1 , wherein the reaction step (a) is performed at a temperature within a range from 10° C. to 40° C.

16. The process according to claim 1 , wherein the phase transfer catalyst comprises tributylmethylammonium chloride.

Assignees

• Basf Se

Inventors

• Saelinger Daniel
• Muelheims Philip
• Zech Helmut
• Goetz Roland

Classifications

• C07C43/176

  having unsaturation outside the aromatic rings · CPC title

• C07C41/01

  Preparation of ethers · CPC title

• C07C41/16 Primary

  by reaction of esters of mineral or organic acids with hydroxy or O-metal groups · CPC title

• C07C43/166

  having unsaturation outside the aromatic rings · CPC title