反応 #1563924

反応方程式

(2,2-dimethoxyethoxy)cyclohexane

sulfuric acid

→

title compound

収率 51.0%

2-(cyclohexyloxy)acetaldehyde

収率 51.0%

溶媒

water

反応条件

後処理

1. 1
   温度Cool the mixture to room temperature
2. 2
   抽出extract the aqueous layer with TBME (2×75 mL)
3. 3
   洗浄Wash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. 4
   乾燥Dry the organic phase over MgSO4
5. 5
   ろ過filter
6. 6
   濃縮concentrate the filtrate under reduced pressure

実験手順

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).

出典