Ethanol → 3-Ethoxy-3-oxo-2-phenylpropanoic acid

Phenylmalonic acid (13.5 g, 0.07 mol) in dry ether (40 mL) was treated with thionyl chloride (8.92 g, 5.4 mL, 0.07 mol) and one drop of N,N-dimethylformamide. The mixture was heated at 40°-50° C. for 3 hours. The clear solution was evaporated under reduced pressure to remove any residual thionyl chloride. The oily residue was redissolved in dry ether (40 mL), the solution was treated with ethanol (0.075 mol, 4.1 mL) and refluxed for 2 hours. The reaction mixture was cooled to room temperature and washed with water. The organic layer was extracted with saturated solution of sodium bicarbonate until alkaline. The combined extracts were washed with ether and the aqueous layer was acidified with 5N HCl to pH 1. The precipitated oil was extracted with CH2Cl2 (50 mL×3). The combined extracts were washed with water (50 mL×4) and dried over anhydrous MgSO4. The oily product crystallized on standing.

1. temperatureThe mixture was heated at 40°-50° C. for 3 hours
2. customThe clear solution was evaporated under reduced pressure
3. customto remove any residual thionyl chloride
4. dissolutionThe oily residue was redissolved in dry ether (40 mL)
5. temperaturerefluxed for 2 hours
6. washwashed with water
7. extractionThe organic layer was extracted with saturated solution of sodium bicarbonate until alkaline
8. washThe combined extracts were washed with ether
9. extractionThe precipitated oil was extracted with CH2Cl2 (50 mL×3)
10. washThe combined extracts were washed with water (50 mL×4)
11. dry with materialdried over anhydrous MgSO4
12. customThe oily product crystallized

ORD record

ord-d0d304e48bc64f40b143545cd4b9d69b

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05418244