Hydrogen Peroxide → HCID 68559856, compound

HRID 19439Notes

Reaction equation

HRID 19439 reaction equation
[CH3:1][O:2][C:3]1[CH:44]=[C:43]([O:45][CH3:46])[CH:42]=[C:41]([O:47][CH3:48])[C:4]=1/[CH:5]=[CH:6]/[CH:7]([S:16]([CH:18](/[CH:27]=[CH:28]/[C:29]1[C:34]([O:35][CH3:36])=[CH:33][C:32]([O:37][CH3:38])=[CH:31][C:30]=1[O:39][CH3:40])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[OH:49]O>C(O)(=O)C>[CH3:36][O:35][C:34]1[CH:33]=[C:32]([O:37][CH3:38])[CH:31]=[C:30]([O:39][CH3:40])[C:29]=1/[CH:28]=[CH:27]/[CH:18]([S:16]([CH:7](/[CH:6]=[CH:5]/[C:4]1[C:41]([O:47][CH3:48])=[CH:42][C:43]([O:45][CH3:46])=[CH:44][C:3]=1[O:2][CH3:1])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=[O:49])=[O:17])[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 68562786HCID 68562786, compound

Product 1

HCID 68559856HCID 68559856, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

(E)-2,4,6-trimethoxystyryl-4-methoxybenzyl sulfoxide (3 g) is dissolved in glacial acetic acid (30 mL) and cooled to 0° C. To the cooled solution is added hydrogen peroxide (7.5 mL of a 30% solution) to form a reaction mixture. The reaction mixture is heated to reflux temperature and maintained at reflux for 1 hour. After 1 hour, the heated reaction mixture is poured onto crushed water ice (200 g). A solid precipitate is formed. The precipitate is separated by filtration, dried, and recrystallized from 2-propanol to yield the desired (E)-2,4,6-trimethoxystyryl-4-methoxybenzyl sulfone.

Workup

  1. customto form a reaction mixture
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux temperature
  4. temperaturemaintained
  5. temperatureat reflux for 1 hour
  6. customthe heated reaction mixture
  7. additionis poured
  8. customA solid precipitate is formed
  9. customThe precipitate is separated by filtration
  10. customdried
  11. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-f3cda40f4883435b8a54b0a7333eb53d
Source dataset
uspto-grants-2010_06
Patent number
US07744889B2

Reaction notes

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