Benzaldehyde → 2-Benzylidenebutanedioic acid

700 mmol of dimethyl succinate and then 20 ml of methanol are added to 290 mmol of sodium methylate dissolved in 80 ml of methanol. The mixture is brought to reflux, and 236 mmol of benzaldehyde are slowly added, followed by 20 ml of methanol. The mixture is maintained at reflux, with stirring, for one hour, and then 100 ml of methanol are distilled off. 120 ml of water and 120 ml of 10N sodium hydroxide solution are added to the concentrated reaction mixture. The removal of the methanol by distillation is continued. The residue is diluted with 150 ml of water. After the addition of dichloromethane, the diacid is precipitated by the slow addition of 12N hydrochloric acid. The diacid is filtered and washed with dicliloromethane and then with water. Drying yields the expected product.

1. temperatureto reflux
2. temperatureThe mixture is maintained
3. temperatureat reflux
4. distillation100 ml of methanol are distilled off
5. addition120 ml of water and 120 ml of 10N sodium hydroxide solution are added to the concentrated reaction mixture
6. customThe removal of the methanol
7. distillationby distillation
8. additionThe residue is diluted with 150 ml of water
9. additionAfter the addition of dichloromethane
10. customthe diacid is precipitated by the slow addition of 12N hydrochloric acid
11. filtrationThe diacid is filtered
12. washwashed with dicliloromethane
13. customDrying

ORD record

ord-8575df7fc98541db9f042aff411ea8b5

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133454