反应详情

To a solution of dimethyl 5-hydroxyisophthalate (28 g, 133 mmol, 1 eq.) in 1400 mL of dry tetrahydrofuran (THF) at ice-bath temperature, lithium aluminum hydride (LiAlH4 or LAH, 4 eq.) was slowly added with stirring. The resultant mixture was allowed warm to 40° C., stirred at this temperature for 16 hours, and then was added an ammonium chloride (NH4Cl) aqueous solution to quench the reaction. After stirring for 1.5 hours, the mixture was filtered with celite, washed with THF. Organic volatiles were evaporated and the residue was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc three times. The combined EtOAc layers were dried over MgSO4 to give product (5-hydroxy-1,3-phenylene)dimethanol (17 g, 82%).

1. stirringstirred at this temperature for 16 hours
2. customto quench
3. customthe reaction
4. stirringAfter stirring for 1.5 hours
5. filtrationthe mixture was filtered with celite
6. washwashed with THF
7. customOrganic volatiles were evaporated
8. customthe residue was partitioned between water and EtOAc
9. extractionThe aqueous phase was extracted with EtOAc three times
10. dry with materialThe combined EtOAc layers were dried over MgSO4