Dimethylformamide → Naproxen

HRID 1380165Notes

Reaction equation

HRID 1380165 reaction equation
Br[C@@H:2](C)[C:3](OC)(OC)[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[CH:5]=1.[C:21]([O-:24])(=[O:23])C.[K+].CN(C)C=O>O>[CH3:15][O:14][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]=[C:4]([C@H:3]([CH3:2])[C:21]([OH:24])=[O:23])[CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 18602099HCID 18602099, compound

Product 1

HCID 156391NaproxenYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (+)(S)2-bromo-1,1-dimethoxy-1-(6-methoxy-2-naphthyl)-propane (3.39 g; 10 mmol), potassium acetate (1.2 g; 12 mmol), N,N-dimethylformamide (14 ml) and of water (8 ml) is heated at 100° C. under stirring. The reaction mixture is worked up as described in example 1 to provide (+)(S)2-(6-methoxy-2-naphthyl)-propionic acid (2.23 g; 9.7 mmol; yield 97%), m.p. 155°-157° C.

Sources & evidence

ORD record
ord-b13831f088ed4954ad98b5ea335b7ce6
Source dataset
uspto-grants-1986_04
Patent number
US04579968

Reaction notes

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