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

HRID 918015Notes

Reaction equation

HRID 918015 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-52c50935d5844caaba2f4df3dc8197b5
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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