Process for producing glycidyl ether
View Patent ↗A process for producing a glycidyl ether and an optically active compound thereof with high yield and an optically high purity comprising reacting an alcohol with epihalohydrin in a base to thereby produce a glycidyl ether, the reaction performed in a two-layer system of a nonaqueous organic solvent and an aqueous solvent.
1. A process for preparing a glycidyl ether represented by the following formula (3);
wherein Ar is unsubstituted phenyl, phenyl substituted by saturated or unsaturated alkyl, phenyl substituted by alkoxy, or phenyl substituted by halogen, 1-naphthyl or 2-naphthyl, which comprises reacting an alcohol represented by the following formula (1);
ArOH (1)
wherein Ar is the same as defined above, at 0 to 50° C. in the presence of one mole or more than one mole of a base, and a quaternary ammonium salt represented by the following formula (4);
R 1 R 2 R 3 R 4 N + X − (4)
wherein R 1 , R 2 , R 3 and R 4 are the same or different, and are alkyl group, alkenyl group, aralkyl group or aryl group, and X− is chloride ion, bromide ion, iodide ion, hydrogensulfate ion or hydroxide ion, and with one to three moles of epihalohydrin represented by the following formula (2);
wherein X is halogen atom, in a two-layer system of a nonaqueous organic solvent selected from the group consisting of toluene, tert-butylmethyl ether and 1,2-dichloroethane, and an aqueous solvent.
2. The process for preparing glycidyl ether according to claim 1 wherein the epihalohydrin is epichlorohydrin or epibromohydrin.
3. The process for preparing glycidyl ether according to claim 1 wherein the base is an alkali hydroxide.
4. The process for preparing glycidyl ether according to claim 1 wherein the alcohol is unsubstituted phenol, cresol, methoxyphenol, allyloxyphenol or phenol substituted by halogen.
5. The process for preparing glycidyl ether according to claim 4 wherein the alcohol is phenol, 4-fluorophenol, 4-methylphenol, 4-methoxyphenol or 2-allyloxyphenol.
6. The process for preparing optically active glycidyl ether according to claim 1 wherein the epihalohydrin is an optically active compound.
7. The process for preparing glycidyl ether according to claim 2 wherein the base is an alkali hydroxide.
8. The process for preparing glycidyl ether according to claim 2 wherein the alcohol is unsubstituted phenol, cresol, methoxyphenol, allyloxyphenol or phenol substituted by halogen.
9. The process for preparing glycidyl ether according to claim 3 wherein the alcohol is unsubstituted phenol, cresol, methoxyphenol, allyloxyphenol or phenol substituted by halogen.
10. The process for preparing glycidyl ether according to claim 8 wherein the alcohol is phenol, 4-fluorophenol, 4-methylphenol, 4-methoxyphenol or 2-allyloxyphenol.
11. The process for preparing glycidyl ether according to claim 9 wherein the alcohol is phenol, 4-fluorophenol, 4-methylphenol, 4-methoxyphenol or 2-allyloxyphenol.