Methyl Acrylate → HCID 24769631, compound

To a stirred solution of 3-phenyl-1-propanol (1.36 g, 10 mmol) in THF (50 mL) at room temperature was added sodium hydride dispersion in oil (60%, 400 mg) portonwise. The cloudy solution warmed sightly and was stirred at room temperature for 30 minutes, and cooled to 0° in an ice-salt bath. Methyl acrylate (1.1 equivalents) was added, the ice bath was removed and stirring was continued for 30 minutes. The mixture was then cautiously treated with water (10 mL) and stirring was continued at room temperature overnight. The solvents were removed under reduced pressure and the residue was partitioned between water (100 mL) and ether (100 mL). The aqueous portion was made acidic to <pH 1 with concentrated HCl, and extracted with ether(2×50 ml). The ether extract was dried (MgSO4), filtered and evaporated under educed pressure to yield the title compound as a mobile colourless oil (0.684 g, 33%). 1H NMR (CDCl3) δ 9.19 (br s, 1H), 7.4-7.0 (5H, m, ArH), 3.60 (2H, t, J 6.2 Hz, OCH2), 3.36 (2H, t, J 6.2 Hz, OCH2), 2.54 (4H, m, 2×CH2), 1.79 (2H, m, CH2). 13C (CDCl3) δ 177.4, 141.7, 128.4, 128.3, 125.7, 70.1, 65.7, 34.8, 31.4, 32.1, 31.0.

1. temperatureThe cloudy solution warmed sightly
2. temperaturecooled to 0° in an ice-salt bath
3. customthe ice bath was removed
4. stirringstirring
5. waitwas continued for 30 minutes
6. additionThe mixture was then cautiously treated with water (10 mL)
7. stirringstirring
8. waitwas continued at room temperature overnight
9. customThe solvents were removed under reduced pressure
10. customthe residue was partitioned between water (100 mL) and ether (100 mL)
11. extractionextracted with ether(2×50 ml)
12. extractionThe ether extract
13. dry with materialwas dried (MgSO4)
14. filtrationfiltered
15. customevaporated under educed pressure

ORD record

ord-a816f14e00a64333917ef1300ddf7127

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253194B2