Water → 6-Methyl-4-phenyl-3,4-dihydrochromen-2-one

HRID 495170Notes

Reaction equation

HRID 495170 reaction equation
[C:1](O)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([CH3:19])[CH:13]=1.O>C1(C)C=CC=CC=1>[CH3:19][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[O:18][C:1](=[O:10])[CH2:2][CH:3]2[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2879P-CresolHCID 87842-Propenoic acid, 3-phenyl-

Product 1

HCID 37916436-Methyl-4-phenyl-3,4-dihydrochromen-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Cinnamic acid (100 gms) and p-cresol (76.6 gms) were charged to a clean and dry flask under nitrogen and stirred. Concentrated sulphuric acid was slowly charged and the reaction mixture heated to 125° C.-130° C. for 6 hours. After completion of reaction the mixture was cooled to about 60° C. and about 50 ml water and about 300 ml toluene were charged under stirring. The layers were separated. The toluene layer was washed with aqueous saturated solution of sodium bicarbonate and water. The organic layer was dried over sodium sulfate and concentrated under vacuum, at a temperature below 50° C. The residue was stripped with 2×100 ml IPA. The residue was dissolved in 200 ml isopropanol, chilled to 5° C. and stirred for 2 hours. The solids obtained were filtered and dried at about 60° C. for 4-5 hours to give about 135 to 137 gms of the title product.

Workup

  1. customdry flask under nitrogen
  2. additionConcentrated sulphuric acid was slowly charged
  3. temperaturethe reaction mixture heated to 125° C.-130° C. for 6 hours
  4. customAfter completion of reaction the mixture
  5. stirringunder stirring
  6. customThe layers were separated
  7. washThe toluene layer was washed with aqueous saturated solution of sodium bicarbonate and water
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated under vacuum, at a temperature below 50° C
  10. dissolutionThe residue was dissolved in 200 ml isopropanol
  11. temperaturechilled to 5° C.
  12. stirringstirred for 2 hours
  13. customThe solids obtained
  14. filtrationwere filtered
  15. customdried at about 60° C. for 4-5 hours

Sources & evidence

ORD record
ord-1f58c4b19cac4c62a62ebc9780f49808
Source dataset
uspto-grants-2009_05
Patent number
US07538249B2

Reaction notes

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