Acetic Acid → 4-(Acetyloxy)-3-tert-butylbenzoic acid

HRID 257289

Reaction equation

HRID 257289 reaction equation
[C:1]([C:5]1[CH:10]=C(C)[CH:8]=[CH:7][C:6]=1O)([CH3:4])([CH3:3])[CH3:2].C([O:16][C:17](=[O:19])[CH3:18])(=O)C.O=O.[C:22]([OH:25])(=[O:24])[CH3:23]>C([O-])(=O)C.[Co+2].C([O-])(=O)C.[Br-].[Mn+2].[Br-].Br>[C:22]([O:25][C:6]1[CH:7]=[CH:8][C:18]([C:17]([OH:16])=[O:19])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 7918Acetic AnhydrideHCID 170042-tert-Butyl-4-methylphenol

Product 1

HCID 180077364-(Acetyloxy)-3-tert-butylbenzoic acidYield 84.4%

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideCatalystHCID 6277Cobalt diacetateCatalystHCID 6432071Manganese dibromideCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture of 82.0 g of 2-tert-butyl-4-methylphenol, 140.0 g of acetic anhydride and 3.0 g of hydrobromic acid (48%) is heated at 90° C. for 1 hour. 280.0 g of acetic acid, 2.5 g of cobalt(II) acetate (tetrahydrate) and 2.5 g of manganese(II) bromide (tetrahydrate) are added, and oxygen (30 ml/min) is passed through the solution at 110° C. The acetic acid is partially removed by applying a vacuum. The reaction mixture which remains is poured into 500 ml of water and filtered, giving 99.5 g (84%) of the product in the form of colourless crystals having a melting point of from 180° to 182° C.

Workup

  1. customis passed through the solution at 110° C
  2. customThe acetic acid is partially removed
  3. additionThe reaction mixture which remains is poured into 500 ml of water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-27fce9cf87e94677ab6c77efa7f38b23
Source dataset
uspto-grants-1993_11
Patent number
US05261953

Linked notes

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