1,2-Dimethoxyethane → HCID 54154816, compound

HRID 918001Notes

Reaction equation

HRID 918001 reaction equation
Br[CH2:2][C:3]([CH3:11])=[CH:4][CH2:5][O:6][CH2:7][CH:8](C)C.[CH2:12]1[O:20][C:19]2[CH:18]=[CH:17][C:16]([OH:21])=[CH:15][C:14]=2[O:13]1.[OH-].[K+].[CH3:24]OCCOC>>[CH:7]([O:6][CH2:5][CH:4]=[C:3]([CH3:2])[CH2:11][O:21][C:16]1[CH:17]=[CH:18][C:19]2[O:20][CH2:12][O:13][C:14]=2[CH:15]=1)([CH3:8])[CH3:24]

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 14797Potassium HydroxideHCID 68289SesamolHCID 53883097HCID 53883097, compound

Product 1

HCID 54154816HCID 54154816, compound

Procedure

2.21 g (0.01 mol) of 1-bromo-4-isobutoxy-2-methyl-2-butene are added at 0° during the course of 5 minutes to 1.38 g (0.01 mol) of 3,4-methylendioxy-phenol and 0.56 g (0.01 mol) of potassium hydroxide in 40 cc of 1,2-dimethoxyethane. After stirring the reaction mixture at room temperature for 24 hours it is filtered and the solvent is distilled off at reduced pressure. The residue is dissolved in ether, washed with saturated salt solution, dried with sodium sulphate and evaporated. The residue is purified by chromatography on silica gel with hexane/ethyl acetate 9:1. 5-(4-isopropoxy-2-methyl-2-butenyloxy)-1,3-benzodioxol is obtained as colourless oil. nD20 = 1.5150.

Workup

  1. filtrationis filtered
  2. distillationthe solvent is distilled off at reduced pressure
  3. dissolutionThe residue is dissolved in ether
  4. washwashed with saturated salt solution
  5. dry with materialdried with sodium sulphate
  6. customevaporated
  7. customThe residue is purified by chromatography on silica gel with hexane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-39821358f57b4494b5d5bf8adab440d4
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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