Methyl Benzoate → Dibenzoylmethane

HRID 1979839Notes

Reaction equation

HRID 1979839 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:10](OC)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([C:10](=[O:17])[CH2:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 7150Methyl BenzoateHCID 7410Acetophenone

Product 1

HCID 8433DibenzoylmethaneYield 89.2%

Procedure

A mixture containing 6.0 g (0.05 mol) of acetophenone, 40.8 g (0.30 mol) of methyl benzoate, and 3.73 g (0.06 mol) of 90% CaO is heated with stirring at 195°-200° C. for three and one-half hours while under nitrogen. The methanol (3.6 mL) that is distilled during the reaction is collected in a Dean Stark collector. The mixture is cooled, and 100 mL of toluene is added. The resulting mixture is cooled in cold water and acidified with 6N HCl. Stirring is continued until all of the solid is dissolved (ca 30 minutes). The toluene layer is separated and washed with aqueous Na2CO3 and water. Evaporation of the toluene solution gave 10 g of 1,3-diphenyl-1,3-propanedione as an oil representing an 89% yield based on acetophenone.

Workup

  1. temperatureis heated
  2. distillationThe methanol (3.6 mL) that is distilled during the reaction
  3. customis collected in a Dean Stark collector
  4. temperatureThe mixture is cooled
  5. addition100 mL of toluene is added
  6. temperatureThe resulting mixture is cooled in cold water
  7. stirringStirring
  8. dissolutionis dissolved (ca 30 minutes)
  9. customThe toluene layer is separated
  10. washwashed with aqueous Na2CO3 and water
  11. customEvaporation of the toluene solution

Sources & evidence

ORD record
ord-a31dd6fa21ce4249bb632e527ab8a026
Source dataset
uspto-grants-1984_11
Patent number
US04482745

Reaction notes

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