Methanol → 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 NCl 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-8225a48c2e3f4d1598e170bfc5b087b1

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05618826