Sodium Hydroxide → 5-Allyloxy-isophthalic acid monomethyl ester

HRID 2216750Notes

Reaction equation

HRID 2216750 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]([O:17][CH3:18])=[O:16])[CH:8]=[C:9]([CH:14]=1)[C:10]([O:12]C)=[O:11])[CH:2]=[CH2:3].[OH-].[Na+]>CO>[CH2:1]([O:4][C:5]1[CH:14]=[C:9]([CH:8]=[C:7]([C:15]([O:17][CH3:18])=[O:16])[CH:6]=1)[C:10]([OH:12])=[O:11])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10933919Dimethyl 5-(allyloxy)isophthalate

Product 1

HCID 219425375-Allyloxy-isophthalic acid monomethyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of dimethyl 5-allyloxy-isophthalate (3.7 g, 14.9 mmol) in methanol (75 mL) was treated with 1M sodium hydroxide (13.4 mL, 13.4 mmol) and the reaction stirred at room temperature for 16 hours. The mixture was concentrated under vacuum and the resulting residue was dissolved in water. The aqueous layer was washed with ethyl acetate (3×), and then acidified (pH 1) by the addition of aqueous HCl. The aqueous solution was then extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to afford 2.6 g (74%) of 3-allyloxy-5-(methoxycarbonyl)benzoic acid.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe resulting residue was dissolved in water
  3. washThe aqueous layer was washed with ethyl acetate (3×)
  4. additionby the addition of aqueous HCl
  5. extractionThe aqueous solution was then extracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d0142b44e9c54bfe8a40a140bc7802f6
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

Loading…