Sulfuric Acid → Methyl cumate

HRID 1405676Notes

Reaction equation

HRID 1405676 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].S(=O)(=O)(O)O.O.NN.[C:21](=O)([O-])O.[Na+]>CO>[CH3:2][CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:21])=[O:9])=[CH:6][CH:5]=1)[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 108204-Isopropylbenzoic AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 227855Methyl cumate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-isopropylbenzoic acid (10 g) and sulfuric acid (5 mL) in methanol (50 mL) was heated under reflux overnight, hydrazine monohydrate (3.66 g) was added, and the mixture was heated under reflux overnight. The reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (10.32 g) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperaturethe mixture was heated
  4. temperatureunder reflux overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0524172f39740c488696322ff07a096
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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