Reaction #1563924

Reaction equation

(2,2-dimethoxyethoxy)cyclohexane

sulfuric acid

→

title compound

Yield 51.0%

2-(cyclohexyloxy)acetaldehyde

Yield 51.0%

Solvents

water

Conditions

Workup

1. 1
   TemperatureCool the mixture to room temperature
2. 2
   Extractionextract the aqueous layer with TBME (2×75 mL)
3. 3
   WashWash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. 4
   DryingDry the organic phase over MgSO4
5. 5
   Filtrationfilter
6. 6
   Concentrationconcentrate the filtrate under reduced pressure

Procedure

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).

Source