Methanol → HCID 22259697, compound

Temperature

41.79999923706055 °C

A one liter four-necked cylindrical shaped reaction flask equipped with a Dean-Stark trap, condenser, thermometer, nitrogen inlet, and a mechanical stirrer was charged with 42 g of D-sorbitol (0.23 mole), 700 mL of cyclohexane, 105 g of 3-bromo-4-ethylbenzaldehyde (0.46 moles), 80 mL of methanol, and 2.5 g of water. The system was then flushed with argon and heated in an oil bath with stirring. The mixture was then heated to a vapor temperature of 41.8° C., at which time 3.0 g of p-toluenesulfonic acid in 40 mL of methanol was slowly added. The reaction was seeded with 1.0 g of 3,4-dimethylbenzylidene sorbitol in 20 mL of methanol. The reaction was then stirred and heated (to about 120° C.) under reflux with removal of water through the Dean Stark trap as cyclohexane was returned to the system. Heating was then recommenced until the vapor temperature reached 70° C., at which time 40 mL of methanol were added slowly. The reaction mixture was allowed to heat up to the same vapor temperature and methanol was added slowly again, and repeated another 5 times. The reaction product (a white gel) was then cooled, neutralized with potassium hydroxide (7 g in 40 mL of methanol), and stripped of the resultant cyclohexane layer (by azeotrope with water). The gel remaining was then filtered and purified in boiling water and boiling methanol, giving 3-bromo-4-isopropylbenzaldehyde as a white solid (108.5 g, 78% yield)(as determined through standard analyses) exhibiting a peak melting transition of 216.3° C. by DSC at 20° C./min.

1. customA one liter four-necked cylindrical shaped reaction flask equipped with a Dean-Stark trap, condenser
2. customThe system was then flushed with argon
3. temperatureheated in an oil bath
4. additionwas slowly added
5. stirringThe reaction was then stirred
6. temperatureheated (to about 120° C.)
7. temperatureunder reflux with removal of water through the Dean Stark trap as cyclohexane
8. temperatureHeating
9. customreached 70° C., at which time 40 mL of methanol
10. additionwere added slowly
11. temperatureto heat up to the same vapor temperature and methanol
12. additionwas added slowly again
13. temperatureThe reaction product (a white gel) was then cooled
14. filtrationThe gel remaining was then filtered
15. custompurified

ORD record

ord-d6ec9c5e08a8421c912ca98f8f30ea2f

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06984740B2