Acetic Anhydride → 3,5-Dimethyl-4-acetoxybenzoic acid

HRID 1846269Notes

Reaction equation

HRID 1846269 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:12].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:13]([O:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][C:10]=1[CH3:11])(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 1383874-Hydroxy-3,5-dimethylbenzoic acid

Product 1

HCID 187041893,5-Dimethyl-4-acetoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 4-hydroxy-3,5-dimethyl-benzoic acid (1) (5.41 g, 32.5 mmol) in anhydrous pyridine (50 mL) were added acetic anhydride and 4-dimethylaminopyridine (0.1 g, 0.8 mmol). The reaction mixture was stirred at room temperature for 16 hours. Pyridine was evaporated under reduced pressure. The residue was taken in ethyl acetate (300 mL). The organic phase was washed with 2 N aq. HCl (100 mL), water (2×100 mL), brine (100 mL) and dried over anhydrous Na2SO4. Solvent was evaporated to give 4-acetoxy-3,5-dimethylbenzoic acid (2) as an off-white solid. Yield: 6.65 g (98%).

Workup

  1. customPyridine was evaporated under reduced pressure
  2. washThe organic phase was washed with 2 N aq. HCl (100 mL), water (2×100 mL), brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customSolvent was evaporated

Sources & evidence

ORD record
ord-cbb30603696647319e30c9716d9ea7b9
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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