Formaldehyde → 2-Nitro-2-(4-octylphenethyl)propane-1,3-diol

Temperature

2.5 °C

3-nitro-1-(4-octylphenyl)propan-1-one (20 g) and dichloromethane (100 mL) are charged into a round bottom flask at 25-30° C. and stirred. The mixture is cooled to −10° C. to 0° C. and triethylsilane (19.9 g) is added. A solution of titanium tetrachloride (19.57 g) in dichloromethane (100 mL) is added over a period of 15 minutes and the obtained reaction mixture is maintained at −10 to 0° C. for 5 hours. Water (200 mL) precooled to 0-10° C. is slowly added to the reaction mixture over a period of 20 minutes and the temperature is allowed to raise to 25-30° C. The reaction mixture is stirred for about 1 hour, organic layer is separated, washed with 5% sodium bicarbonate solution (100 mL), followed by 20% brine solution (100 mL), the organic layer is concentrated under vacuum at 45° C. to obtain 38.2 g of crude 1-(3-nitropropyl)-4-octylbenzene. Toluene (200 mL) and crude 1-(3-nitropropyl)-4-octylbenzene (38.2 g) are charged into the round bottom flask at 25-30° C. and stirred. Potassium carbonate (18.96 g) and paraformaldehyde (7.21 g) are charged and the reaction mixture is stirred at the same temperature for about 6 hours. The reaction mixture is filtered and washed with toluene (40 mL). The obtained filtrate, water (200 mL) and ethyl acetate (60 mL) are charged into a round bottom flask and stirred for 2 hours. The organic layer is separated, washed with 5% hydrochloric acid solution (100 mL), 5% sodium bicarbonate solution (100 mL) and followed by 5% brine solution (100 mL). The resultant organic layer is concentrated under vacuum at below 45° C. n-Hexane (100 mL) is added to the obtained compound and stirred. The obtained mixture is cooled to 0 to 5° C., maintained at the same temperature for about 60 minutes, filtered and washed with n-hexane (20 mL). The obtained wet compound and toluene (80 mL) are charged into a round bottom flask, heated to 40-45° C. and maintained at the same temperature for about 15 minutes. The reaction mixture is cooled to 0-5° C., maintained for about 45 minutes, filtered and washed the product with toluene (40 mL) precooled to 0-5° C. and the product obtained is dried under vacuum at 25-30° C. to give the title compound.

1. stirringthe reaction mixture is stirred at the same temperature for about 6 hours
2. filtrationThe reaction mixture is filtered
3. washwashed with toluene (40 mL)
4. additionThe obtained filtrate, water (200 mL) and ethyl acetate (60 mL) are charged into a round bottom flask
5. stirringstirred for 2 hours
6. customThe organic layer is separated
7. washwashed with 5% hydrochloric acid solution (100 mL), 5% sodium bicarbonate solution (100 mL)
8. concentrationThe resultant organic layer is concentrated under vacuum at below 45° C. n-Hexane (100 mL)
9. additionis added to the obtained compound
10. stirringstirred
11. temperaturemaintained at the same temperature for about 60 minutes
12. filtrationfiltered
13. washwashed with n-hexane (20 mL)
14. additionThe obtained wet compound and toluene (80 mL) are charged into a round bottom flask
15. temperatureheated to 40-45° C.
16. temperaturemaintained at the same temperature for about 15 minutes
17. temperatureThe reaction mixture is cooled to 0-5° C.
18. temperaturemaintained for about 45 minutes
19. filtrationfiltered
20. washwashed the product with toluene (40 mL)
21. customprecooled to 0-5° C.
22. customthe product obtained
23. customis dried under vacuum at 25-30° C.

ORD record

ord-309fc25867bf4269b155cb9fe6dda777

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216943B2