تفاعل #1941410

معادلة التفاعل

(2,2-dimethoxyethoxy)cyclohexane

sulfuric acid

→

title compound

المردود 51.0%

2-(cyclohexyloxy)acetaldehyde

المردود 51.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةCool the mixture to room temperature
2. 2
   استخلاصextract the aqueous layer with TBME (2×75 mL)
3. 3
   غسيلWash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. 4
   تجفيفDry the organic phase over MgSO4
5. 5
   ترشيحfilter
6. 6
   تركيزconcentrate the filtrate under reduced pressure

الإجراء التجريبي

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).

المصدر