Sodium Hydroxide → 5-Acetyl-2-ethoxybenzoic acid

HRID 412041Notes

Reaction equation

HRID 412041 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-ethoxy-benzoate (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 colourless solid (5.4 g, 60%), m.p. 122-125° C.

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-0c9ac649db7544f38062708bd542fb80
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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