Sodium Hydroxide → (4-Acetyl-3-hydroxy-2-propylphenoxy)acetic acid

HRID 652502Notes

Reaction equation

HRID 652502 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([OH:16])[C:8]=1[CH2:17][CH2:18][CH3:19])C.[OH-].[Na+]>CO>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:20])=[O:3])=[C:8]([CH2:17][CH2:18][CH3:19])[C:9]=1[OH:16])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13389144Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate

Product 1

HCID 13753869(4-Acetyl-3-hydroxy-2-propylphenoxy)acetic acidYield 82.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5.6 g of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid ethyl ester in 50 ml of methanol was added 50 ml of 1.0N sodium hydroxide and the solution was stirred at reflux for 2 hours. The methanol was removed in vacuo, the residue was acidified and the product was extracted with ether. The dried (over magnesium sulfate) extract was concentrated in vacuo to a solid which was recrystallized from ether-hexane to give 4.18 g of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid, the titled compound, mp 128°-130°, (83% yield).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe methanol was removed in vacuo
  3. extractionthe product was extracted with ether
  4. dry with materialThe dried (over magnesium sulfate)
  5. extractionextract
  6. concentrationwas concentrated in vacuo to a solid which
  7. customwas recrystallized from ether-hexane

Sources & evidence

ORD record
ord-6e24e712a5d54b51bda708d08bd1aee4
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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