Potassium Hydroxide → Ethyl 2-benzylacrylate

A mixture of 8.5 g of KOH in 100 ml of ethanol was added at room temperature to 40 g of benzylmalonic acid diethyl ester in 80 ml of ethanol. The mixture was stirred overnight at room temperature, then concentrated by evaporation, thereafter 14 ml of water was added and then the mixture was acidified in an ice bath with 12.6 ml of concentrated hydrochloric acid. Partitioning between water and ether was carried out, the organic phase was dried and the ether was distilled off. Then, 26 ml of pyridine, 1.22 g of piperidine and 3.56 g of paraformaldehyde were added to the residue. The mixture was heated in an oil bath (130° ) for 90 minutes, cooled, 440 ml of water was added and extraction was carried out 3 times with 150 ml of n-hexane. The combined organic phases were washed alternatively with water, 1N HCl, water, saturated NaHCO3 solution and brine. The solution was dried (MgSO4) and evaporated to give the title compound as colorless oil (26 g, 85% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure.

1. concentrationconcentrated by evaporation
2. addition14 ml of water was added
3. customthe mixture was acidified in an ice bath with 12.6 ml of concentrated hydrochloric acid
4. customPartitioning between water and ether
5. customthe organic phase was dried
6. distillationthe ether was distilled off
7. additionThen, 26 ml of pyridine, 1.22 g of piperidine and 3.56 g of paraformaldehyde were added to the residue
8. temperatureThe mixture was heated in an oil bath (130° ) for 90 minutes
9. temperaturecooled
10. addition440 ml of water was added
11. extractionextraction
12. washThe combined organic phases were washed alternatively with water, 1N HCl, water, saturated NaHCO3 solution and brine
13. dry with materialThe solution was dried (MgSO4)
14. customevaporated

ORD record

ord-f0e003cf152a4b52ba09ddcfaeb8f965

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05314920