Hydrochloric Acid → 4-Acetylbenzoic Acid

HRID 1715506Notes

Reaction equation

HRID 1715506 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH3:4].Cl>CO.O1CCOCC1>[C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 137990Methyl 4-acetylbenzoate

Product 1

HCID 114704-Acetylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

A solution of NaOH (1.7 g/12 ml) was added to methyl 4-acetylbenzoate (5.04 g, 28.3 mmol) in MeOH-dioxane (2:1, 60 ml). After stirring at room temperature for 12 hr, the mixture was acidified with 5N HCl, and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4. Evaporation of solvent gave 4-acetylbenzoic acid as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-05cea0ff2673480aafb68563d040f5a0
Source dataset
uspto-grants-2010_09
Patent number
US07799818B2

Reaction notes

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