Sulfuric Acid → 2-Benzoylcyclohexanone

HRID 2188358Notes

Reaction equation

HRID 2188358 reaction equation
CCC([O-])(C)C.[Na+].[C:8](OC)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:18]1(=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.S(=O)(=O)(O)O>C1(C(C)C)C=CC=CC=1>[C:8]([CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C:18]1=[O:24])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7150Methyl BenzoateHCID 7967CyclohexanoneHCID 2733478Sodium 2-methylbutan-2-olate

Product 1

HCID 2756272-BenzoylcyclohexanoneYield 76%

Reagents, catalysts & solvents 1

HCID 7406CumeneSolvent

Conditions

Temperature
100 °C

Procedure

Cumene (dry, 180 mL), sodium tert-pentoxide (35.8 g; 0.326 mol), and methyl benzoate (68.1 g; 0.50 mol) were placed into a four-necked, round bottom, half-liter flask equipped with a stirrer, a thermometer, and a reflux condenser. The mixture was heated to 100° C. and kept at that temperature under a blanket of nitrogen. Cyclohexanone (24.5 g; 0.250 mol) was added slowly over a period of 15 minutes by means of a syringe pump. After 20 minutes from the beginning of the addition of the ketone, the mixture was cooled with an ice water bath to room temperature. Aqueous sulfuric acid (10%) was added with stirring, keeping the temperature below 25° C., until the pH of the aqueous layer was acidic. The organic layer was washed in a one liter separation funnel with aqueous sodium bicarbonate and then with water. The solvents were evaporated on a Rotovap and the residue was crystallized from heptane, affording BCH (38.43 g, 76% yield) having a purity of 99% (GC).

Workup

  1. customequipped with a stirrer
  2. temperaturethe mixture was cooled with an ice water bath to room temperature
  3. customthe temperature below 25° C.
  4. washThe organic layer was washed in a one liter separation funnel with aqueous sodium bicarbonate
  5. customThe solvents were evaporated on a Rotovap
  6. customthe residue was crystallized from heptane
  7. customaffording BCH (38.43 g, 76% yield)

Sources & evidence

ORD record
ord-71a8c18f726049c1aeabf777cecf25bc
Source dataset
uspto-grants-2002_06
Patent number
US06410795B1

Reaction notes

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