반응 #1563924

반응 방정식

(2,2-dimethoxyethoxy)cyclohexane

sulfuric acid

→

title compound

수율 51.0%

2-(cyclohexyloxy)acetaldehyde

수율 51.0%

용매

water

반응 조건

후처리

1. 1
   온도Cool the mixture to room temperature
2. 2
   추출extract the aqueous layer with TBME (2×75 mL)
3. 3
   세척Wash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. 4
   건조Dry the organic phase over MgSO4
5. 5
   여과filter
6. 6
   농축concentrate the filtrate under reduced pressure

실험 절차

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).

출처