Benzenepropanoic acid → Methyl 3-phenylpropionate

Hydrocinnamic acid (10.0 g, 66.6 mmol, 1 eq.) was dissolved in methanol (90 ml), conc. H2SO4 (1 ml) added dropwise with stirring and the reaction mixture was stirred under reflux for 5 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in water (100 ml) and extracted with EtOAc (3×50 ml). The combined organic phases were washed with 10% NaHCO3 aq. (2×50 ml), brine (50 ml) before being dried (MgSO4), filtered and concentrated to give the title compound 82 (10.8 g, 99%) as a clear, colourless oil. Analytical data consistent with the literature (Black, P. J. et al., Eur. J. Org. Chem. 4367-4378 (2006)).

1. stirringthe reaction mixture was stirred
2. temperatureunder reflux for 5 h
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in water (100 ml)
5. extractionextracted with EtOAc (3×50 ml)
6. washThe combined organic phases were washed with 10% NaHCO3 aq. (2×50 ml), brine (50 ml)
7. dry with materialbefore being dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-8cf550506c124c8787707e53a89be0ab

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242954B2