Piperonyl alcohol → HCID 53854790, compound

HRID 1284221Notes

Reaction equation

HRID 1284221 reaction equation
[Br:1][CH2:2][CH:3]=[CH:4][CH2:5]Br.[Na].[CH2:8]1[O:18][C:17]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=2[O:9]1>COCCOC>[Br:1][CH2:2][CH:3]=[CH:4][CH2:5][O:14][CH2:13][C:12]1[CH:15]=[CH:16][C:17]2[O:18][CH2:8][O:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 10322Piperonyl alcoholHCID 131802-Butene, 1,4-dibromo-HCID 5360545Sodium

Product 1

HCID 53854790HCID 53854790, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

11.8 g (0.055 mol) of 1,4-dibromo-2-butene and 8.7 g (0.05 mol) of sodium salt of 3,4-methylendioxy-benzylalcohol are covered with a layer of 100 cc of 1,2-dimethoxyethane. The mixture is stirred at 20°-25° for 16 hours and at 50° for 15 minutes. The solvent is subsequently distilled off at reduced pressure, the residue is taken up in ether and the ether solution is extracted with water. The organic phase is dried with sodium sulphate and the ether is then distilled off and the residue is chromatographed on silica gel with hexane/ethyl acetate 9 : 1. The chromatographically uniform 5-[(4-bromo-2-butenyloxy)-methyl]-1,3-benzodioxol is obtained as slightly yellow oil.

Workup

  1. distillationThe solvent is subsequently distilled off at reduced pressure
  2. extractionthe ether solution is extracted with water
  3. dry with materialThe organic phase is dried with sodium sulphate
  4. distillationthe ether is then distilled off
  5. customthe residue is chromatographed on silica gel with hexane/ethyl acetate 9 : 1

Sources & evidence

ORD record
ord-27655f8f81864b8bac429c19ea68a8cf
Source dataset
uspto-grants-1976_08
Patent number
US03978134

Reaction notes

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