Sodium Hydroxide → HCID 13912815, compound

HRID 652516Notes

Reaction equation

HRID 652516 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[C:14]([OH:21])[C:13]=2[CH2:22][CH2:23][CH3:24])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[CH:5][CH:6]=2)=[C:13]([CH2:22][CH2:23][CH3:24])[C:14]=1[OH:21])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13912814HCID 13912814, compound

Product 1

HCID 13912815HCID 13912815, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.30 g 4-[(4-acetyl-3-hydroxy-2-propylphenoxy)methyl]benzoic acid methyl ester and 48 mL of 1.0 N sodium hydroxide dissolved in 100 mL of methanol was stirred at reflux for 1.25 hour. The solvent was removed in vacuo and the reaction mixture was acidified with 6 N hydrochloric acid. The product was extracted with ethyl acetate and the dried (over magnesium sulfate) extract was concentrated in vacuo to give a solid. Recrystallization from acetonehexane gave 2.613 g, mg 187°-189°, (83% yield) of 4-[(4-acetyl-3-hydroxy-2-propylphenoxy)methyl]benzoic acid, the title compound.

Workup

  1. temperatureat reflux for 1.25 hour
  2. customThe solvent was removed in vacuo
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialthe dried (over magnesium sulfate)
  5. extractionextract
  6. concentrationwas concentrated in vacuo
  7. customto give a solid
  8. customRecrystallization from acetonehexane

Sources & evidence

ORD record
ord-950d6a5244ee458a9231afd39d4e6841
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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