Carbon Dioxide → p-Methoxyphenylpropionic acid

Temperature

-78 °C

1-(2,2-dibromovinyl)-4-methoxybenzene (17.38 g, 59.5 mmol) prepared in Reference Synthetic Example 1 was dissolved in tetrahydrofuran (230 ml) in nitrogen atmosphere, and a 2.59 mol/l n-butyllithium/hexane solution was dropwise added at −78° C. After the dropwise addition, the solution was returned to 0° C. and stirred for 90 minutes, and then cooled to −78° C. again, and crushed dry ice was added. After stirring for 30 minutes, water was added to the solution and the solution was concentrated under reduced pressure. The residue was diluted with diethyl ether, and extracted with a 1 mol/l sodium hydroxide aqueous solution twice. The obtained aqueous layer was acidified (pH=1) with hydrochloric acid and extracted with ethyl acetate twice. The obtained organic layer was washed with water and a saturated salt solution, dried over anhydrous sodium sulfate, subjected to filtration and concentrated under reduced pressure to give the desired compound (4-methxoyphenyl)propionic acid (9.73 g, 93%) as crude crystals.

1. additionAfter the dropwise addition
2. customwas returned to 0° C.
3. additionwas added
4. stirringAfter stirring for 30 minutes
5. concentrationthe solution was concentrated under reduced pressure
6. additionThe residue was diluted with diethyl ether
7. extractionextracted with a 1 mol/l sodium hydroxide aqueous solution twice
8. extractionextracted with ethyl acetate twice
9. washThe obtained organic layer was washed with water
10. dry with materiala saturated salt solution, dried over anhydrous sodium sulfate
11. filtrationsubjected to filtration
12. concentrationconcentrated under reduced pressure

ORD record

ord-04314678c6b84df8a840ed9ccd0da5d4

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07595415B2