Sodium Carbonate → 1,2-Epoxy-3,4-(dimethylmethylenedioxy)-5-hexene

HRID 1741950Notes

Reaction equation

HRID 1741950 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]([OH:22])[CH:13]2[O:19][C:18]([CH3:21])([CH3:20])[O:17][CH:14]2[CH:15]=[CH2:16])(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[O:22]1[CH:12]([CH:13]2[O:19][C:18]([CH3:20])([CH3:21])[O:17][CH:14]2[CH:15]=[CH2:16])[CH2:11]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 190109853,4-(Dimethylmethylenedioxy)-2-hydroxy-5-hexen-1-yl p-toluenesulfonate

Product 1

HCID 100123231,2-Epoxy-3,4-(dimethylmethylenedioxy)-5-hexeneYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4-(Dimethylmethylenedioxy)-2-hydroxy-5-hexen-1-yl p-toluenesulfonate (17.88 g) was dissolved in ml of methanol, and 17.11 g of anhydrous sodium carbonate was added at room temperature, followed by stirring the mixture for 15 minutes. The reaction mixture was filtered through Celite, and crystals were washed with diethyl ether. After the filtrate was concentrated, the solid was filtered through a silica gel column. The filtrate was concentrated under reduced pressure to obtain 7.87 g of 1,2-epoxy-3,4-(dimethylmethylenedioxy)-5-hexene having the following properties.

Workup

  1. additionwas added at room temperature
  2. filtrationThe reaction mixture was filtered through Celite, and crystals
  3. washwere washed with diethyl ether
  4. concentrationAfter the filtrate was concentrated
  5. filtrationthe solid was filtered through a silica gel column
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f33abe414fcb46f6954500ae52f20fcb
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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