Azobisisobutyronitrile → Ethyl 2-(3-formylphenyl)acetate

Temperature

100 °C

N-bromosuccinimide (1.78 g) and 2,2′-azobis(2-methylpropionitrile) (16 mg) were added to a solution of ethyl-3-methylphenylacetate (1.76 mL) in chloroform (18 mL) and heated to reflux for 3 hours. On cooling the mixture was diluted with chloroform (40 mL), washed sequentially with saturated aqueous sodium bicarbonate solution (2×50 mL), brine (50 mL), dried (sodium sulfate) and concentrated. The residue was dissolved in nitrogen degassed dimethylsulfoxide (50 mL) and sodium bicarbonate (13.5 g) added. The mixture was heated at 100° C., under nitrogen for 30 min. The reaction was cooled in an ice-bath and poured into brine (300 mL). The aqueous phase was extracted with diethyl ether (3×300 mL). The combined organics were dried (sodium sulfate) and concentrated. Purification on silica, eluting with 10% diethyl ether in iso-hexane, to afford the subtitle compound as a yellow oil (1.23 g).

1. temperatureheated
2. temperatureto reflux for 3 hours
3. temperatureOn cooling the mixture
4. washwashed sequentially with saturated aqueous sodium bicarbonate solution (2×50 mL), brine (50 mL)
5. dry with materialdried (sodium sulfate)
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in nitrogen
8. customdegassed dimethylsulfoxide (50 mL) and sodium bicarbonate (13.5 g)
9. additionadded
10. temperatureThe reaction was cooled in an ice-bath
11. additionpoured into brine (300 mL)
12. extractionThe aqueous phase was extracted with diethyl ether (3×300 mL)
13. dry with materialThe combined organics were dried (sodium sulfate)
14. concentrationconcentrated
15. customPurification on silica
16. washeluting with 10% diethyl ether in iso-hexane

ORD record

ord-22f7d069446142a18a2f621d7c5b1010

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951954B2