Sulfuric Acid → 3-(Acetyloxy)-4-methylbenzoic acid

HRID 23953

Reaction equation

HRID 23953 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[C:17](OC(=O)C)(=[O:19])[CH3:18]>O>[C:17]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 685123-Hydroxy-4-methylbenzoic acid

Product 1

HCID 225699983-(Acetyloxy)-4-methylbenzoic acidYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-hydroxy-4-methylbenzoic acid (3.0 g, 19.7 mmol) in acetic anhydride (5.6 mL) was treated with sulfuric acid (0.03 mL), heated to 70° C., cooled and diluted with water. The resulting solid was collected by filtration yielding 1.14 g (30%) of the title compound, which was used without further purification.

Workup

  1. temperaturecooled
  2. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-7908a31fbbb64d2282804f5d3fcaa166
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Linked notes

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