Diethyl Ether → 3-Methoxy-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, 0.071 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) and the solution was treated with methyl alcohol (0.075. mol, 3 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 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. additionthe solution was treated with methyl alcohol (0.075. mol, 3 mL)
6. temperaturerefluxed for 2 hours
7. washwashed with water
8. extractionThe organic layer was extracted with saturated solution of sodium bicarbonate until alkaline
9. washThe combined extracts were washed with ether
10. extractionThe precipitated oil was extracted with CH2Cl2 (50 ml×3)
11. washThe combined extracts were washed with water (50 mL×4)
12. dry with materialdried over anhydrous MgSO4
13. customThe oily product crystallized

ORD-Eintrag

ord-0da4f2d719d242edb0f08c1b08e2f0c2

Quelldatensatz

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05610188