Benzene → 3,5-Dimethyl-4-acetoxybenzoic acid

HRID 2288249Notes

Reaction equation

HRID 2288249 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17])[C:11]([OH:13])=[O:12].[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[CH3:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([CH3:18])[C:16]=1[O:17][C:19](=[O:21])[CH3:20])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7918Acetic AnhydrideHCID 1383874-Hydroxy-3,5-dimethylbenzoic acid

Product 1

HCID 187041893,5-Dimethyl-4-acetoxybenzoic acidYield 56.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 60 ml of benzene was suspended 10 g/60 mmol of 3,5-dimethyl-4-hydroxybenzoic acid, and 7.5 g/74 mmol of acetic anhydride and 150 μl of pyridine were added to the suspension. The reaction mixture was refluxed under heat for 12 hours, and allowed to stand at room temperature for 12 hours. The precipitated crystals were separated by filtration and washed with a small amount of benzene and air dried to obtain 7.1 g of the desired 3,5-dimethyl-4-acetoxybenzoic acid. 1H-NMR (CDCl3): δ2.22 (6H, s), 2.37 (3H, s), 7.85 (2H, s), 11.53 (1H, s).

Workup

  1. additionwere added to the suspension
  2. temperatureThe reaction mixture was refluxed
  3. temperatureunder heat for 12 hours
  4. customThe precipitated crystals were separated by filtration
  5. washwashed with a small amount of benzene and air
  6. customdried

Sources & evidence

ORD record
ord-9a8cec86e9094caca2e2c5b113049324
Source dataset
uspto-grants-2000_07
Patent number
US06087502

Reaction notes

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