Ethanol → HCID 131732562, compound

HRID 873512Notes

Reaction equation

HRID 873512 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([B:11]([OH:13])[OH:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])=O.[CH3:14][C:15]1([CH3:23])[CH2:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[CH2:16]1.[CH2:24]([C:36]1[CH:41]=CC=C[C:37]=1S(O)(=O)=O)[CH2:25][CH2:26]CCCCCCCCC.[CH2:46]([OH:48])[CH3:47]>O>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([B:11]([OH:13])[OH:12])=[CH:4][C:3]=1[CH:1]1[C:26]2[C:46](=[O:48])[CH2:47][C:36]([CH3:41])([CH3:37])[CH2:24][C:25]=2[O:21][C:19]2[CH2:20][C:15]([CH3:23])([CH3:14])[CH2:16][C:17](=[O:22])[C:18]1=2

Participants

6

Reactant 4

HCID 702EthanolHCID 25457Dodecylbenzenesulphonic acidHCID 31358DimedoneHCID 2759225(3-Formyl-4-methoxyphenyl)boronic acid

Product 1

HCID 131732562HCID 131732562, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(3-Formyl-4-methoxyphenyl)boronic acid (5.30 g, 29.5 mmol) and 5,5-dimethylcyclohexane-1,3-dione (8.26 g, 58.9 mmol) were added to a suspension of dodecylbenzenesulfonic acid (0.96 g, 2.94 mmol) in water (196 ml) at room temperature, and the mixture thus obtained was then stirred under heating to reflux for 5 hours. After air-cooling, a solid was collected from the reaction solution by filtration. The solid thus obtained was suspended in ethanol, and the solution thus obtained was then stirred under heating to reflux. After air-cooling, the solvent was distilled away from the reaction solution under reduced pressure. Diethyl ether was added to the residue thus obtained, and the solid thus generated was collected by filtration and was then dried to obtain the title compound (7.99 g, yield: 64%).

Workup

  1. customthe mixture thus obtained
  2. temperatureunder heating
  3. temperatureto reflux for 5 hours
  4. temperatureAfter air-cooling
  5. filtrationa solid was collected from the reaction solution by filtration
  6. customThe solid thus obtained
  7. customthe solution thus obtained
  8. stirringwas then stirred
  9. temperatureunder heating to reflux
  10. temperatureAfter air-cooling
  11. distillationthe solvent was distilled away from the reaction solution under reduced pressure
  12. additionDiethyl ether was added to the residue
  13. customthus obtained
  14. filtrationthe solid thus generated was collected by filtration
  15. customwas then dried

Sources & evidence

ORD record
ord-fd19bbf8aa1449699f9f22bc48134c02
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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