Water → 5-Acetyl-2-ethoxybenzoic acid

HRID 21955Notes

Reaction equation

HRID 21955 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 1 with 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 from ethyl acetate to give the title compound as a colourless solid (5.4 g, 60%), m.p. 122°-135° 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 from ethyl acetate

Sources & evidence

ORD record
ord-76f36cac73e448d590f3ee43106bec8c
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

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