4-Hydroxybenzaldehyde → HCID 54541004, compound

HRID 1731151Notes

Reaction equation

HRID 1731151 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 hours. 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 reflexed with stirring for 2 hours. After cooling, filtration and washed 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% 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, ethanol (460 ml)
  6. customA crystalline solid is formed
  7. filtrationcollected by filtration
  8. temperatureAfter cooling
  9. filtrationfiltration
  10. washwashed with ether

Sources & evidence

ORD record
ord-d6191f17ce074daa8a3b0c6ba6e3293b
Source dataset
uspto-grants-1976_11
Patent number
US03995033

Reaction notes

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