Reacción #1563924

Ecuación de reacción

(2,2-dimethoxyethoxy)cyclohexane

sulfuric acid

→

title compound

Rendimiento 51.0%

2-(cyclohexyloxy)acetaldehyde

Rendimiento 51.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaCool the mixture to room temperature
2. 2
   Extracciónextract the aqueous layer with TBME (2×75 mL)
3. 3
   LavadoWash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. 4
   SecadoDry the organic phase over MgSO4
5. 5
   Filtraciónfilter
6. 6
   Concentraciónconcentrate the filtrate under reduced pressure

Procedimiento

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).

Fuente