Water → 5-Acetyl-2-ethoxybenzoic acid

HRID 327069Notes

Reaction equation

HRID 327069 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[O:13][CH2:14][CH3:15].[OH-].[Na+].O>O1CCOCC1>[C:10]([C:8]1[CH:7]=[CH:6][C:5]([O:13][CH2:14][CH3:15])=[C:4]([CH:9]=1)[C:3]([OH:16])=[O:2])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18536574Methyl 5-acetyl-2-ethoxybenzoate

Product 1

HCID 185365885-Acetyl-2-ethoxybenzoic acidYield 60.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-acetyl-2-ethoxybenzoic acid methyl ester (9.6 g, 0.043 mol), 5M aqueous sodium hydroxide solution (44 ml, 0.217 mol), water (80 ml) and 1,4-dioxan (80 ml) was stirred at room temperature for 18 hours. The solvent was removed by evaporation under vacuum, the residue dissolved in water (100 ml) and the resulting solution acidified to pH 1with concentrated hydrochloric acid. The aqueous mixture was extracted with ethyl acetate (4×100 ml) and the combined extracts dried (Na2SO4) and evaporated under vacuum. The resulting solid was crystallised form ethyl acetate to give the title compound as a colourless solid (5.4 g, 60%), m.p. 122°-125° C. Found: C,63.20; H,5.81. C11H12O4 requires C,63.45; H,5.81%.

Workup

  1. customThe solvent was removed by evaporation under vacuum
  2. dissolutionthe residue dissolved in water (100 ml)
  3. extractionThe aqueous mixture was extracted with ethyl acetate (4×100 ml)
  4. dry with materialthe combined extracts dried (Na2SO4)
  5. customevaporated under vacuum
  6. customThe resulting solid was crystallised form ethyl acetate

Sources & evidence

ORD record
ord-0e998a6c697c447f8f0c7e954fad31bb
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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