2-(6-methoxynaphthalen-2-yl)prop-2-enoic Acid → Naproxen

HRID 1088493Notes

Reaction equation

HRID 1088493 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[CH2:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2.[H][H]>CO>[CH3:17][C@H:13]([C:14]([OH:16])=[O:15])[C:8]1[CH:7]=[CH:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 37179052-(6-methoxynaphthalen-2-yl)prop-2-enoic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 156391NaproxenYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml autoclave, the inside atmosphere of which had previously been replaced with argon, were placed 0.45 g (2 mmoles) of 6-methoxy-α-methylene-2-naphthaleneacetic acid and 20 ml of methanol. Then, 2.0 mg (0.002 mmole) of Ru((-)-T-BINAP)(O2CCF3)2 prepared in Referential Example 4 was added to the mixture to perform hydrogenation for 24 hours at a hydrogen pressure of 40 kg/cm2 and at a reaction temperature of 20° C. Thereafter, the solvent was distilled off to provide 0.43 g of naproxen. The yield thereof was 93.7%.

Workup

  1. additionwas added to the mixture
  2. customfor 24 hours
  3. customat a reaction temperature of 20° C
  4. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-0625824e3c594985b6aa270c07dc9050
Source dataset
uspto-grants-1990_10
Patent number
US04962230

Reaction notes

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