Sodium Hydroxide → 5-Allyloxy-isophthalic acid monomethyl ester

HRID 431855Notes

Reaction equation

HRID 431855 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-fe1cc8be63634c61b94936efe3556219
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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