Methanol → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 1907022Notes

Reaction equation

HRID 1907022 reaction equation
C1(C)C=CC(S(O[CH:11](C)[C:12](OC)(OC)[C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[CH:14]=2)(=O)=O)=CC=1.CO.[C:33](=[O:36])(O)[O-:34].[Na+]>O>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([CH:12]([CH3:11])[C:33]([OH:34])=[O:36])[CH:22]=[CH:21]2

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 200291641,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate

Product 1

HCID 13022-(6-Methoxy-2-naphthyl)propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of the oil, 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate, from Example 30, 50 ml of water, 100 ml of methanol and 19.5 g of sodium bicarbonate is refluxed (70° C.) for 14 hours. After that time, the mixture is cooled, poured into 6 volumes of water and extracted twice with 100 ml of toluene. The aqueous layer is acidified with concentrated hydrochloric acid to a pH of about 3 to yield 4.8 g of 2-(6-methoxy-2-naphthyl)propionic acid (melting point: 151.5°-153° C.).

Workup

  1. temperatureAfter that time, the mixture is cooled
  2. extractionextracted twice with 100 ml of toluene

Sources & evidence

ORD record
ord-cd1bd1810f6442ba96b3f5b6b762e561
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

Loading…