Methanol → 2-(6-Methoxy-2-naphthyl)propionic acid
Reaction equation
CS(O[CH:6](C)[C:7](OC)(OC)[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]=1)(=O)=O.[C:25](=[O:28])(O)[O-:26].[Na+].CO>O>[CH3:19][O:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:7]([CH3:6])[C:25]([OH:26])=[O:28])[CH:17]=[CH:16]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture is prepared from the oil, 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate, from Example 16, 20 g of sodium bicarbonate, 200 ml of methanol and 150 ml of water, and the mixture is heated at 70° C. with reflux for 14 hours. The methanol is removed under reduced pressure on a rotary evaporator and the oil remaining is extracted with ethyl ether. The organic and aqueous phases are separated and the aqueous phase is acidified with hydrochloric acid to afford 12.5 g of 2-(6-methoxy-2-naphthyl)propionic acid.
Workup
- temperaturewith reflux for 14 hours
- customThe methanol is removed under reduced pressure on a rotary evaporator
- extractionthe oil remaining is extracted with ethyl ether
- customThe organic and aqueous phases are separated
Sources & evidence
- ORD record
- ord-846f1d603ea846358be1ccd12ef4ae36
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04654438
Reaction notes
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