2-Butene, 1,4-dibromo- → HCID 54088028, compound

HRID 1284220Notes

Reaction equation

HRID 1284220 reaction equation
[Na].[CH2:2]1[O:10][C:9]2[CH:8]=[CH:7][C:6]([OH:11])=[CH:5][C:4]=2[O:3]1.[Br:12][CH2:13][CH:14]=[CH:15][CH2:16]Br>COCCOC>[Br:12][CH2:13][CH:14]=[CH:15][CH2:16][O:11][C:6]1[CH:7]=[CH:8][C:9]2[O:10][CH2:2][O:3][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 131802-Butene, 1,4-dibromo-HCID 68289SesamolHCID 5360545Sodium

Product 1

HCID 54088028HCID 54088028, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6.4 g (0.04 mol) of sodium salt of 3,4-methylendioxyphenol are added at -20° to a solution of 8.6 g (0.04 mol) of 1,4-dibromo-2-butene in 100 cc of 1,2-dimethoxyethane. The mixture is stirred at 0° for 3 hours and subsequently at room temperature for 1 hour. The solvent is distilled off at reduced pressure and the residue is taken up in ether. The ether solution is extracted with saturated salt solution, is dried with sodium sulphate and evaporated. The residue is purified by chromatography on silica gel with hexane/ethyl acetate 9 : 1. The 5-(4-bromo-2-butenyloxy)-1,3-benzodioxol is obtained as colourless oil.

Workup

  1. distillationThe solvent is distilled off at reduced pressure
  2. extractionThe ether solution is extracted with saturated salt solution
  3. dry with materialis dried with sodium sulphate
  4. customevaporated
  5. customThe residue is purified by chromatography on silica gel with hexane/ethyl acetate 9 : 1

Sources & evidence

ORD record
ord-a6b51b0bba61434f83488d7c84d1aa73
Source dataset
uspto-grants-1976_08
Patent number
US03978134

Reaction notes

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