Hydrochloric Acid → Dibenzoylmethane

HRID 77685

Reaction equation

HRID 77685 reaction equation
CO.[Na].[C:4]([O:12]C)(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[CH3:15].Cl>C1(C)C(C)=CC=CC=1>[C:17]1([C:14](=[O:16])[CH2:15][C:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:12])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7150Methyl BenzoateHCID 7410AcetophenoneHCID 5360545Sodium

Product 1

HCID 8433DibenzoylmethaneYield 63.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methanol (0.26 ml, 6.4 mmol) and sodium (0.14 g, 6.1 mmol) were combined in xylene (60 ml) and stirred for 20 min at room temperature. Methyl benzoate (49, 2.47 ml, 19.7 mmol) and acetophenone (0.58 ml, 5.0 mmol) were added and the mixture stirred for 6 hr at 140° C. The mixture was cooled to room temperature and hydrochloric acid (10 ml, 6 N) was added and stirred for 15 min. The resulting mixture was extracted into ethyl acetate, washed twice with water, twice with saturated sodium bicarbonate and twice with water. The ethyl acetate was dried over magnesium sulfate, filtered and evaporated to afford an oil. The crude oil was chromatographed on silica gel with ethyl acetate/hexane to give a solid. The solid was recrystallized from methanol to give 0.71 g (63%) of a pink-orange solid: mp 70-71° C. [expected mp 77-78° C.]; 1H NMR: δ 6.85 (s, 1H), 7.51 (m, 6H), 7.98 (d, 4H, J=6.8 Hz); 13C NMR: δ 93.1, 127.1, 128.6, 132.4, 135.5, 185.6.

Workup

  1. stirringthe mixture stirred for 6 hr at 140° C
  2. temperatureThe mixture was cooled to room temperature
  3. stirringstirred for 15 min
  4. extractionThe resulting mixture was extracted into ethyl acetate
  5. washwashed twice with water, twice with saturated sodium bicarbonate and twice with water
  6. dry with materialThe ethyl acetate was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto afford an oil
  10. customThe crude oil was chromatographed on silica gel with ethyl acetate/hexane
  11. customto give a solid
  12. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-114bd565d6e04be79770afa8564843f5
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Linked notes

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