Methyltriphenylphosphonium iodide → Benzoic acid, 3-ethenyl-, methyl ester

Temperature

-50 °C

To a stirred suspension of 590 mg of methyl triphenylphosphonium iodide in 50 ml of dry tetrahydrofuran cooled to -50° C. was added dropwise 5.3 ml of 2.5M n-butyl lithium in hexane. The resulting mixture was allowed to warm to 0° C. over a period of one hour. The mixture was then cooled to -70° C. and 2.0 g of methyl 3-formylbenzoate in 20 ml of dry tetrahydrofuran was added dropwise over a period of 20 minutes. The reaction mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was concentrated in vacuo and the residue treated with water (200 ml) and extracted with diethyl ether (2×200 ml). The extracts were combined, washed with water and a brine solution and dried over magnesium sulfate. Removal of the solvent gave 2 g of an oil which was flash chromatographed on silica gel (30% ethyl acetate--hexane; v:v) , 2.0 g. Distillation in vacuo gave 1.36 g.

1. temperatureto warm to 0° C. over a period of one hour
2. temperatureThe mixture was then cooled to -70° C.
3. temperatureto warm to room temperature
4. concentrationThe reaction mixture was concentrated in vacuo
5. additionthe residue treated with water (200 ml)
6. extractionextracted with diethyl ether (2×200 ml)
7. washwashed with water
8. dry with materiala brine solution and dried over magnesium sulfate
9. customRemoval of the solvent

ORD record

ord-49f91237c0ec474190352220462b1ff4

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05322847