Hydrochloric Acid → isobutyl (S)-2-(6-methoxy-2-naphthyl)propionate

HRID 3978

Reaction equation

HRID 3978 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@H:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2.Cl>C(O)C(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14]([O:16][CH2:4][CH:5]([CH3:10])[CH3:6])=[O:15])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 156391Naproxen

Product 1

HCID 54469957isobutyl (S)-2-(6-methoxy-2-naphthyl)propionate

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A solution of 300 mg of (S)-2-(6-methoxy-2-naphthyl)propionic acid in 5 ml of isobutyl alcohol is saturated with hydrogen chloride. After 24 hours, the excess alcohol is distilled off in vacuo and the residue is purified by chromatography using an alumina substrate to yield isobutyl (S)-2-(6-methoxy-2-naphthyl)propionate.

Workup

  1. distillationthe excess alcohol is distilled off in vacuo
  2. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-8b2fe1a99b9b4f7d9bf65ad29d804e7a
Source dataset
uspto-grants-1988_02
Patent number
US04723033

Linked notes

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