反应 #312592

反应方程式

1,2,6-trihydroxyhexane

benzaldehyde dimethylacetal

→

title product

收率 66.3%

4-[(2-Phenyl)-1,3-dioxolan-4-yl]-1-butanol

收率 66.3%

溶剂

DMF

ethyl acetate

反应条件

后处理

1. 1
   温度cooled
2. 2
   过滤filtered
3. 3
   浓缩The filtrate was concentrated
4. 4
   其他residue obtained
5. 5
   洗涤After being washed with water and brine
6. 6
   干燥the solution was dried over Na2SO4
7. 7
   其他The crude product obtained
8. 8
   其他after evaporation of the solvent
9. 9
   其他was chromatographed on silica eluting with ethyl acetate

实验过程

To a solution of 1,2,6-trihydroxyhexane (10.0 g, 74.6 mmol) and benzaldehyde dimethylacetal (15.0 g, 98.7 mmol) in dry DMF (10 mL) was added Amberlyst 15 (5.0 g). The mixture was stirred at 100° C. for 5 min, then cooled and filtered. The filtrate was concentrated and residue obtained was re-dissolved in ethyl acetate. After being washed with water and brine, the solution was dried over Na2SO4. The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate. Concentration of the proper fractions afforded 11.0 g (66%) of the title product (a mixture of diastereomers) as a colorless oil: 1H NMR (CDCl3, 300 MHz, ppm) 7.48 (m, 2H), 7.39 (m, 3H), 5.92 (s, 0.4H), 5.80 (s, 0.6H), 4.3-4.1 (m, 2H), 3.64 (m, 3H), 1.8-1.4 (m, 6H).

来源