4-Hydroxybenzaldehyde → HCID 54541004, compound

HRID 2397169Notes

Reaction equation

HRID 2397169 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[C:14]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[C:12]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:11]=1[C:34](=[O:36])[CH3:35])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1.Cl>C(OCC)(=O)C>[OH:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[CH:35][C:34]([C:11]2[C:12]([O:25][C:26](=[O:33])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:13][C:14]([O:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:10]=2[O:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:36])=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric Acid2×HCID 3092602-Acetylbenzene-1,3,5-triyl tribenzoate

Product 1

HCID 54541004HCID 54541004, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2',4',6'-tribenzoyloxyacetophenone (83.5 g) and 4-hydroxybenzaldehyde are dissolved in 850 ml of ethyl acetate. Hydrogen chloride is led in at a temperature of 0° for 6 h. The reaction mixture is then kept at about 5° for 4 days and then freed from most of the hydrogen chloride with nitrogen passed through the solution. The ethyl acetate is evaporated and the residue mixed with 300 ml benzene and evaporated to remove the remaining hydrogen chloride. The residue is mixed with abs. ethanol (460 ml). A crystalline solid is formed, collected by filtration and then suspended in ether and refluxed with stirring for 2 h. After cooling, filtration and washing with ether there is obtained 41 g of 4-hydroxy-2',4',6'-tribenzoyloxy-chalcone with m.p. 198°-200°. This compound is dissolved in 1400 ml dioxane and hydrogenated at room temperature and atmospheric pressure with 4 g of 10 percent Pd/C as catalyst. When the theoretical amount of hydrogen has been absorbed the reaction is stopped, the catalyst removed by filtration and the dioxane evaporated in vacuo. The residue is recrystallized twice from abs. ethanol and 28 g of 3-(4-hydroxyphenyl)-2',4',6'-tribenzoyloxypropiophenone is obtained with a m.p. of 156°-8°.

Workup

  1. customThe ethyl acetate is evaporated
  2. additionthe residue mixed with 300 ml benzene
  3. customevaporated
  4. customto remove the remaining hydrogen chloride
  5. additionThe residue is mixed with abs
  6. customA crystalline solid is formed
  7. filtrationcollected by filtration
  8. temperaturerefluxed
  9. temperatureAfter cooling
  10. filtrationfiltration
  11. washwashing with ether

Sources & evidence

ORD record
ord-99b1060fc51642978d5e2bae25d80505
Source dataset
uspto-grants-1977_05
Patent number
USRE029202

Reaction notes

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