Carbon Dioxide → 3,4-Dimethoxybenzonitrile

3,4-Dimethoxy-benzaldehyde (287 g, 1.73 moles) in ethanol (1 liter) is treated with a solution of hydroxylamine hydrochloride (147 g, 2.12 moles) in water (200 ml) followed by addition of 17N sodium hydroxide (150 ml). The reaction mixture is stirred overnight at room temperature, poured on ice, and solid carbon dioxide is added until the solution is neutral. Extraction with methylene chloride followed by drying and evaporation of the extracts gives an orange oil. Distilled acetic anhydride (410 g, 4.0 moles) is added dropwise to the oil. When the addition is complete, the mixture is heated at reflux for 0.5 hour, poured into water and stirred for 0.5 hour. The reaction mixture is extracted with diethyl ether and the organic extract is dried and evaporated to give an orange oil. The oil is distilled at 135°-140° C/0.5 mm and dissolved in methylene chloride. The solution is washed with 2N sodium hydroxide, dried and evaporated to give the title compound; nmr (CDCl3) δ 3.94 (s, 6H) and 7.2 (m, 3H). EXAMPLE 2

1. additionis added until the solution
2. extractionExtraction with methylene chloride
3. customby drying
4. customevaporation of the extracts
5. customgives an orange oil
6. additionWhen the addition
7. temperaturethe mixture is heated
8. temperatureat reflux for 0.5 hour
9. stirringstirred for 0.5 hour
10. extractionThe reaction mixture is extracted with diethyl ether
11. extractionthe organic extract
12. customis dried
13. customevaporated
14. customto give an orange oil
15. distillationThe oil is distilled at 135°-140° C/0.5 mm
16. dissolutiondissolved in methylene chloride
17. washThe solution is washed with 2N sodium hydroxide
18. customdried
19. customevaporated

ORD record

ord-1f8ecf508515483b85acfaca3b857e88

Source dataset

uspto-grants-1978_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04108997