Sodium Hydroxide → 5-Acetyl-2-ethoxybenzoic acid

HRID 374786Notes

Reaction equation

HRID 374786 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH3:16])=[C:8]([CH:13]=1)[C:9]([O:11]C)=[O:10])(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH3:16])=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 2

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

Product 1

HCID 185365885-Acetyl-2-ethoxybenzoic acidYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of methyl 5-acetyl-2-ethoxybenzoate (9.6 g, 0.043 mol) in a mixture of 1,4-dioxane (80 ml) and water (80 ml) was treated with 5N aqueous sodium hydroxide solution (44 ml, 0.217 mol). The mixture was stirred at room temperature for 18 hours then the solvents evaporated under vacuum. The residue was dissolved in water (100 ml), then this solution was acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate (4×100 ml). The organic extracts were combined, dried (Na2SO4) and evaporated under vacuum. Crystallization of the residue from ethyl acetate gave the title compound as a colorless 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 solvents evaporated under vacuum
  2. dissolutionThe residue was dissolved in water (100 ml)
  3. extractionextracted with ethyl acetate (4×100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated under vacuum
  6. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-bb4d63f2a2864c57a91dfe26848c0f47
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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