Methanol → Methyl 3-phenoxypropionate

Temperature

0 °C

3-Phenoxypropionic acid (10.0 g, 60 mmol) was dissolved in methanol (100 mL) . The reaction mixture was allowed to cool to 0° C. and SOCl2 was slowly added over a 15 min period. The reaction mixture was slowly allowed to warm to room temperature over a 2 h period. The reaction mixture was concentrated in vacuo, then redissolved in ethyl acetate (100 mL). The organic layer was washed with water (2×150 mL), dried (MgSO4), concentrated in vacuo to provide crude product in 95% yield. 1H NMR (CDCl3) δ2.84 (t, J=6.4 Hz, 2H), 3.76 (s, 3H), 4.28 (t, J=6.4 Hz, 2H), 6.95 (m, 3H), 7.31 (m, 2H).

1. temperatureto warm to room temperature over a 2 h period
2. concentrationThe reaction mixture was concentrated in vacuo
3. dissolutionredissolved in ethyl acetate (100 mL)
4. washThe organic layer was washed with water (2×150 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customto provide crude product in 95% yield

ORD record

ord-64496545ec074ad6965aaaff4670aac2

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06469008B2