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

HRID 1283490Notes

Reaction equation

HRID 1283490 reaction equation
[OH-].[K+].CO.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[CH:11]=[CH:10]2>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2732945ethyl 2-(6-methoxynaphthalen-2-yl)propanoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 6.0 g. of potassium hydroxide, 6 ml. of water and 60 ml. of methanol is added to the ethyl 2-(6-methoxy-2-naphthyl)propionate, and the mixture is heated at reflux for 45 minutes, cooled to ambient temperature, acidified and mixed with 60 ml. of water. Methanol is removed by evaporation in vacuo, and the resultant solution is extracted with two 60 ml. portions of methylene chloride. The combined methylene chloride extracts are evaporated to dryness to yield 2-(6-methoxy-2-naphthyl)propionic acid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 45 minutes
  3. additionmixed with 60 ml
  4. customMethanol is removed by evaporation in vacuo
  5. extractionthe resultant solution is extracted with two 60 ml
  6. customThe combined methylene chloride extracts are evaporated to dryness

Sources & evidence

ORD record
ord-9a54e741558a45d5bcf86225f95d8818
Source dataset
uspto-grants-1976_08
Patent number
US03975432

Reaction notes

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