反应详情

A stirred mixture of nonanedioic acid (18.8 g; 0.10 mol), benzyl alcohol (10.8 g; 0.10 mol), and p-toluenesulphonic acid (0.2 g) in toluene (200 mL) was refluxed through a Dean-Stark trap overnight. The mixture was cooled to ambient temperature and extracted with 10% aqueous N-methyl-D-glucamine (4×25 mL). The last extract was a milky emulsion. The first three extracts were combined, acidified with 1 M HCl (50 mL), and filtered to give recovered nonanedioic acid (3.8 g). The emulsion was acidified with 1 M HCl and allowed to separate overnight. The organic layer was evaporated and the residue dissolved in hexane (200 mL) and diethyl ether (50 mL). The solution was extracted with 10% N-methyl-D-glucamine (2×50 mL) (emulsions broken by adding a little ethanol). The organic solution was washed with water (1×25 mL) and the combined aqueous solution was acidified with 1 M HCl (150 mL). After extraction with dichloromethane-tetrahydrofuran (4:1) (5×10 mL), the combined extracts were dried (Na2SO4), filtered, and evaporated. 13.0 g (47%) product was obtained (oil that solidified on standing).

1. temperaturewas refluxed through a Dean-Stark trap overnight
2. extractionextracted with 10% aqueous N-methyl-D-glucamine (4×25 mL)
3. extractionThe last extract
4. filtrationfiltered
5. customto give
6. customrecovered nonanedioic acid (3.8 g)
7. customto separate overnight
8. customThe organic layer was evaporated
9. dissolutionthe residue dissolved in hexane (200 mL)
10. extractionThe solution was extracted with 10% N-methyl-D-glucamine (2×50 mL) (emulsions
11. additionby adding a little ethanol)
12. washThe organic solution was washed with water (1×25 mL)
13. extractionAfter extraction with dichloromethane-tetrahydrofuran (4:1) (5×10 mL)
14. dry with materialthe combined extracts were dried (Na2SO4)
15. filtrationfiltered
16. customevaporated