反应详情

温度

50 °C

82.3 g (229 mmole) 7-(4′-tert-Butyl-phenyl)-2-cyclohexylmethyl-indan-1-one were dissolved in 292 ml toluene in a 1 l-roundbottom flask equipped with a reflux condenser. 9.5 g (1.1 eq.) sodium borohydride were added. Then 40 ml (4.3 eq.) methanol were added at 50° C. and the mixture was stirred for 3 h at 50° C. An additional 1 g of sodium borohydride and 5 ml methanol were added and the mixture was stirred another 2 h at 50° C. 2M sulphuric acid was added until the gas evolution ceased. After addition of 100 ml water the layers were separated and the organic layer was washed two times with 2M sulphuric acid and once with a saturated sodium chloride solution. The solvent was evaporated and the crude indanol was dissolved in approx. 350 ml of toluene. After addition of 0.7 g p-toluene sulfonic acid the mixture was heated to reflux using a Dean-Stark-trap until TLC showed complete conversion (90 min). The solution was washed twice with a saturated NaHCO3-solution, once with water and once with a saturated sodium chloride solution. Drying over magnesium sulphate, evaporation of the solvent and crystallization from 800 ml ethanol afforded 67.3 g (86%) of the desired indene as white crystals. 1H-NMR (400 MHz, CDCl3): δ=7.45, 7.33, 7.25, 7.14 (4×m, 7H, aromatic), 6.69 (s, 1H, ═CH), 3.35 (s, 2H, benzylic), 2.34 (d, 2H, aliphatic), 1.71-1.50 (m, 6H, aliphatic), 1.39 (s, 9H, C(CH3)3), 1.24-0.87 (m, 5H, aliphatic) ppm.

1. customequipped with a reflux condenser
2. stirringthe mixture was stirred another 2 h at 50° C
3. customwere separated
4. washthe organic layer was washed two times with 2M sulphuric acid
5. customThe solvent was evaporated
6. dissolutionthe crude indanol was dissolved in approx. 350 ml of toluene
7. additionAfter addition of 0.7 g p-toluene sulfonic acid the mixture
8. temperaturewas heated
9. temperatureto reflux
10. customconversion (90 min)
11. washThe solution was washed twice with a saturated NaHCO3-solution, once with water and once with a saturated sodium chloride solution
12. dry with materialDrying over magnesium sulphate, evaporation of the solvent and crystallization from 800 ml ethanol