Реакция #635374

Уравнение реакции

2-Hydroxy-1-phenylethanone

ethylene glycol

→

(2-phenyl-[1,3]dioxolan-2-yl)methanol

Выход 98.0%

Растворители

benzene

Условия реакции

Обработка

1. 1
   Другоеequipped with a Dean-Stark
2. 2
   Температураheated
3. 3
   Температураto reflux for 24 hours
4. 4
   ДругоеThe solvent was evaporated in vacuo, water and ethyl acetate
5. 5
   workup.ADDITIONwere added to the resulting residue
6. 6
   Другоеthe organic layer was separated
7. 7
   ЭкстракцияAn aqueous layer was further extracted with ethyl acetate twice
8. 8
   Промывкаwashed with a saturated saline solution
9. 9
   СушкаIt was dried over anhydrous sodium sulfate
10. 10
    Другоеthe solvent was evaporated
11. 11
    Другоеin vacuo and the resulting crude product was purified by a silica gel column chromatography (toluene:ethyl acetate=4:1)

Методика

2-Hydroxy-1-phenylethanone (49.39 g, 297 mmol), ethylene glycol (84 mL, 1500 mmol), p-toluenesulfonic acid monohydrate (1.0 g) and benzene (500 mL) were added to a one-liter eggplant type flask equipped with a Dean-Stark dehydrating device and heated to reflux for 24 hours. The solvent was evaporated in vacuo, water and ethyl acetate were added to the resulting residue and the organic layer was separated. An aqueous layer was further extracted with ethyl acetate twice and the organic layers were combined and washed with a saturated saline solution. It was dried over anhydrous sodium sulfate, the solvent was evaporated therefrom in vacuo and the resulting crude product was purified by a silica gel column chromatography (toluene:ethyl acetate=4:1) to give (2-phenyl-[1,3]dioxolan-2-yl)methanol (52.30 g, 98%) as an oily product. 1H-NMR (DMSO-d6) δ: 3.51 (d, J=6.4 Hz, 2H), 3.74-3.78 (m, 2H), 4.01-4.05 (m, 2H), 4.09 (t, J=6.4 Hz, 1H), 7.28-7.36 (m, 3H), 7.40-7.43 (m, 2H).

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