Реакция #1563924

Уравнение реакции

(2,2-dimethoxyethoxy)cyclohexane

sulfuric acid

→

title compound

Выход 51.0%

2-(cyclohexyloxy)acetaldehyde

Выход 51.0%

Растворители

water

Условия реакции

Обработка

1. 1
   ТемператураCool the mixture to room temperature
2. 2
   Экстракцияextract the aqueous layer with TBME (2×75 mL)
3. 3
   ПромывкаWash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. 4
   СушкаDry the organic phase over MgSO4
5. 5
   Фильтрацияfilter
6. 6
   Концентрированиеconcentrate the filtrate under reduced pressure

Методика

Acidify a mixture of (2,2-dimethoxyethoxy)cyclohexane and water (30 mL) to a pH of 1.0 with sulfuric acid (9.0 M aqueous solution), and connect the mixture to a short-path distillation head. Reduce the pressure to 26.7 kPa and heat the mixture to 100° C. for 1 h. Cool the mixture to room temperature, then extract the aqueous layer with TBME (2×75 mL). Wash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL). Dry the organic phase over MgSO4, filter, and concentrate the filtrate under reduced pressure to furnish the title compound (634 mg, 51% yield). 1H NMR (400 MHz, CDCl3): δ 9.73 (t, J=1.0 Hz, 1H), 4.06 (d, J=1.0 Hz, 2H), 3.31 (tt, J=9.2, 3.9 Hz, 1H), 1.95-1.89 (m, 2H), 1.79-1.68 (m, 2H), 1.57-1.50 (m, 1H), 1.39-1.20 (m, 5H).

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