Piperonyl alcohol → HCID 53700017, compound

HRID 918014Notes

Reaction equation

HRID 918014 reaction equation
[Na].[CH2:2]1[O:12][C:11]2[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=2[O:3]1.[Br:13][CH2:14][C:15]([CH3:19])=[CH:16][CH2:17]Br>COCCOC>[Br:13][CH2:14][C:15]([CH3:19])=[CH:16][CH2:17][O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:11]2[O:12][CH2:2][O:3][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 10322Piperonyl alcoholHCID 20585818860-95-2HCID 5360545Sodium

Product 1

HCID 53700017HCID 53700017, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

8.7 g (0.05 mol) of sodium salt of the 3,4-methylendioxybenzylalcohol are added at 0° during the course of 15 minutes and while stirring to 12.5 g (0.055 mol) of 1,4-dibromo-2-methyl-2-butene which is dissolved in 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 then distilled off at reduced pressure and 100 cc amounts of water and ether are added to the residue. The aqueous phase is separated in a separatory funnel, the ether phase is extracted with saturated salt solution, is dried with sodium sulphate and evaporated. The residue is chromatographed on silica gel with hexane/ethyl acetate 9:1, whereby the 5-[(4-bromo-3-methyl-2-butenyloxy)-methyl]-1,3-benzodioxol is obtained as uniform colourless oil.

Workup

  1. distillationThe solvent is then distilled off at reduced pressure and 100 cc amounts of water and ether
  2. additionare added to the residue
  3. customThe aqueous phase is separated in a separatory funnel
  4. extractionthe ether phase is extracted with saturated salt solution
  5. dry with materialis dried with sodium sulphate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with hexane/ethyl acetate 9:1, whereby the 5-[(4-bromo-3-methyl-2-butenyloxy)-methyl]-1,3-benzodioxol
  8. customis obtained as uniform colourless oil

Sources & evidence

ORD record
ord-2153e432d0354693a29e547557d73ac0
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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