Sodium Sulfate → HCID 13548392, compound

HRID 638667Notes

Reaction equation

HRID 638667 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:17](=[O:34])[CH:18]([CH3:33])[CH:19]([CH3:32])[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)=[O:21])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:31][O:30][C:24]1[CH:23]=[C:22]([CH:20]([OH:21])[CH:19]([CH3:32])[CH:18]([CH3:33])[CH:17]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH3:7])[CH:10]=2)[OH:34])[CH:27]=[CH:26][C:25]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 135483901,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethyl-1,4-butanedioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 13548392HCID 13548392, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1 g of lithium aluminum hydride suspended in 100 ml of tetrahydrofuran and cooled to ice temperatures under dry nitrogen was added 3.86 g of the starting diketone, 1,4-bis(3,4-dimethoxyphenyl),2,3-dimethyl butane-1,4-dione, in 30 ml of dry THF. The mixture was allowed to slowly come to room temperature while stirring and finally refluxed for 1 hour and then allowed to stand overnight. One ml of saturated sodium sulfate solution was added dropwise and stirring continued for several hours. Filtration and evaporation gave a colorless oil that crystallized on addition of ether. A yield of 3.93 g (quant.) was obtained. IR spectra showed no carbonyl.

Workup

  1. temperaturecooled to ice temperatures under dry nitrogen
  2. customto slowly come to room temperature
  3. temperaturefinally refluxed for 1 hour
  4. stirringstirring
  5. waitcontinued for several hours
  6. filtrationFiltration and evaporation
  7. customgave a colorless oil that
  8. customcrystallized on addition of ether
  9. customA yield of 3.93 g (quant.) was obtained

Sources & evidence

ORD record
ord-1974e96d04bb43e59f701bc1b498f09f
Source dataset
uspto-grants-1985_12
Patent number
US04562298

Reaction notes

Loading…