反应详情

3-Phenyl-1-indanone (83 g, 0.4 mol) was dried by refluxing in C6H6 (120 ml) with removal of the azeotroped H2O. To this solution was added Et2O (120 ml) and Zn wool (26.25 g, 0.4 mol). The reaction mixture was heated to near reflux and a crystal of I2 added. Ethyl bromoacetate (110 g, 0.6 mol) was added over 2 hours, the temperature being kept near reflux by heat of reaction and some external heating. After the addition, the mixture was stirred and refluxed for a further 0.5 hour, cooled and poured into ice and acetic acid. The mixture was extracted with Et2O. The Et2O was washed with 1% NH4OH, dried (Na2SO4), filtered and evaporated and the residue distilled to give a mixture of ethyl 3-phenylindene-1-acetate and its corresponding double bond isomer (83.6g) b.p. 145°-155° C. (0.1 mm). This mixture of esters was hydrogenated over 10% Pd/C (0.6g) to give ethyl 3-phenylindan-1-acetate. This ester was hydrolyzed by refluxing with sodium hydroxide in ethanol to give the title compound, m.p. 126°-9° C.

1. temperatureThe reaction mixture was heated
2. temperatureto near reflux
3. temperaturenear reflux
4. temperatureby heat of reaction
5. additionAfter the addition
6. temperaturerefluxed for a further 0.5 hour
7. temperaturecooled
8. extractionThe mixture was extracted with Et2O
9. washThe Et2O was washed with 1% NH4OH
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. customevaporated
13. distillationthe residue distilled
14. customto give