Methanol → HCID 11254610, compound

A solution of 2-(3′-benzoyl-2′-acetoxyphenyl)propionic acid (1) (6.2 g) in methanol (35 ml) was added wish concentrated H2SO4 (0.3 ml). The mixture was stirred at room temperature for 15 hours until disappearance (1) and of the reaction intermediates. The solvent was evaporated off under vacuum and the residue was dissolved in ethyl acetate (30 ml) and washed with water. The organic layer was treated with a NaOH solution (100 ml), and the basic phase was acidified with 4N HCl and extracted with ethyl acetate (2×25 ml). The collected organic layers were washed with brine, dried over Na2SO4 and evaporated under vacuum. The crude product (4.3 g) was dissolved in isopropyl ether (5 ml) and the slightly yellow precipitate was filtered. n-Hexane (25 ml) was added to the residue and the mixture was stirred overnight. After filtration, 3.2 g of (2) were obtained (0.11 mol; 70% yield starting from 4) as a whitish solid (melting point 108-111° C.).

1. customThe solvent was evaporated off under vacuum
2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
3. washwashed with water
4. additionThe organic layer was treated with a NaOH solution (100 ml)
5. extractionextracted with ethyl acetate (2×25 ml)
6. washThe collected organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. customevaporated under vacuum
9. dissolutionThe crude product (4.3 g) was dissolved in isopropyl ether (5 ml)
10. filtrationthe slightly yellow precipitate was filtered
11. additionn-Hexane (25 ml) was added to the residue
12. filtrationAfter filtration

ORD record

ord-4b70aa93ce674b8bbd4704b872496585

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06770781B1