Reaktion #1563924

Reaktionsgleichung

(2,2-dimethoxyethoxy)cyclohexane

sulfuric acid

→

title compound

Ausbeute 51.0%

2-(cyclohexyloxy)acetaldehyde

Ausbeute 51.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturCool the mixture to room temperature
2. 2
   Extraktionextract the aqueous layer with TBME (2×75 mL)
3. 3
   WaschenWash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. 4
   TrocknenDry the organic phase over MgSO4
5. 5
   Filtrationfilter
6. 6
   Einengenconcentrate the filtrate under reduced pressure

Vorschrift

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).

Quelle