Sodium Chloride → 1,3-Benzenedimethanol

In a manner similar to that in Example 1, m-xylylene dichloride was converted into m-diacetoxymethylbenzene at 97° to 101° C. in 3 hours by use of a reactant mixture comprising 100 parts of m-xylylene dichloride (97.6% purity), 100 parts of anhydrous sodium acetate, 125 parts of monochlorobenzene, and 2 parts of triethylamine. To the reaction mixture was added 250 parts of warm water to dissolve the by-product sodium chloride. The mixture was left standing at 80° C. to allow it to settle in two layers. To the monochlorobenzene layer which had been freed from the catalyst amine by removing in the same manner as in Example 1, were added 46 parts of sodium hydroxide and 310 parts of water to allow the saponification to proceed at 94° C. for 2 hours. After saponification, the reaction mixture was neutralized with 3N hydrochloric acid and left standing at 82° C. to allow the mixture to settle in two layers. The aqueous layer containing m-xylylene glycol, was added at 80° C. 50 parts of monochlorobenzene to extract impurities. After separation, m-xylylene glycol was extracted from the purified aqueous layer with n-butyl acetate in the same way as in Example 1. The n-butyl acetate layers obtained by repeating batchwise extraction three times were combined, distilled to recover ethyl acetate, and dried in vacuo to obtain 76.0 parts of m-xylylene glycol (melting point, 53.5° - 55° C.) in a yield of 98.7%.

1. waitThe mixture was left
2. customstanding at 80° C.
3. customby removing in the same manner as in Example 1
4. additionwere added 46 parts of sodium hydroxide and 310 parts of water
5. waitleft
6. customstanding at 82° C.
7. additionThe aqueous layer containing m-xylylene glycol
8. additionwas added at 80° C
9. extraction50 parts of monochlorobenzene to extract impurities
10. customAfter separation, m-xylylene glycol
11. extractionwas extracted from the purified aqueous layer with n-butyl acetate in the same way as in Example 1
12. customThe n-butyl acetate layers obtained
13. extractionextraction three times
14. distillationdistilled
15. customto recover ethyl acetate
16. customdried in vacuo

ORD record

ord-fc3ef178a92c4dc2adbe71a3cdd98637

Source dataset

uspto-grants-1976_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03993699