4-(2,2-DIETHOXY-ETHOXY)-BENZONITRILE synthesis
- Product Name:4-(2,2-DIETHOXY-ETHOXY)-BENZONITRILE
- CAS Number:787575-81-9
- Molecular formula:C13H17NO3
- Molecular Weight:235.28
Yield:787575-81-9 71%
Reaction Conditions:
with potassium carbonate in DMF (N,N-dimethyl-formamide) at 85; for 72 h;
Steps:
65 Preparation 65; 4-(2,2-di-ethoxy-ethoxy)-benzonitrile
Powdered potassium carbonate (5.18 g, 37.7 mmol) is added to a stirred solution of 4-cyanophenol (2.00 g, 16.8 mmol) and bromoacetaldehyde diethyl acetal (4.53 mL, 30.3 mmol) in anhydrous DMF (20 mL). The resultant mixture is stirred at 85 °C under nitrogen for 3 days. The mixture is cooled to ambient temperature; then water (100 mL) and EtOAc (100 mL) are added to the mixture. The organic layer is separated, dried over MGS04, filtered and concentrated. The oil is chromatographed on silica (gradient 5-20% EtOAc in hexane) to give 2.80 g (11.9 mmol, 71% yield) of the title COMPOUND. 1H NMR (CDC13) : 61. 24 (t, J= 7.1 Hz, 6H), 3.60-3. 68 (m, 2H), 3.73-3. 81 (m, 2H), 4.04 (d, J = 5.2 Hz, 2H), 4.83 (t, J = 5.2 Hz, 1H), 6.97 (br d, J = 9.2 Hz, 2H), 7.58 (br d, J = 9. 2 Hz, 2H); Analysis for C13HL7NO3 : calcd: C, 66.36 ; H, 7.28 ; N, 5.95 ; found: C, 66. 41 ; H, 7.34 ; N, 6.01.
References:
WO2004/94386,2004,A1 Location in patent:Page 22#78