4-Hydroxybenzaldehyde → P-hydroxyl ethyl cinnaMate

To 20 g of p-hydroxybenzaldehyde and 32.5 g of monoethyl malonate were added 6 ml of pyridine and 0.2 ml of piperidine, then the mixture thus obtained was heated at 100° to 110° C. for 10 hours under stirring. The reaction mixture was then cooled, extracted with chloroform, and the chloroform layer was washed with a saturated aqueous solution of potassium hydrogen sulfite and water in this order, the chloroform extract was dried with magnesium sulfate. The solvent was removed by evaporation and the residue thus obtained was crystallized from isopropyl ether-n-hexane to yield 25.2 g of ethyl 4-hydroxycinnamate. Light yellow indefinite form crystals. Melting point: 70°-71° C.

1. customthe mixture thus obtained
2. temperaturewas heated at 100° to 110° C. for 10 hours
3. temperatureThe reaction mixture was then cooled
4. extractionextracted with chloroform
5. washthe chloroform layer was washed with a saturated aqueous solution of potassium hydrogen sulfite and water in this order
6. extractionthe chloroform extract
7. dry with materialwas dried with magnesium sulfate
8. customThe solvent was removed by evaporation
9. customthe residue thus obtained
10. customwas crystallized from isopropyl ether-n-hexane

ORD record

ord-56183908644b4140bf73ebdc0423dffb

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05137889