Isobutanol → HCID 54408087, compound

HRID 1580736Notes

Reaction equation

HRID 1580736 reaction equation
Br[CH2:2][C:3]([CH3:16])=[CH:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1.[CH2:17]([OH:21])[CH:18]([CH3:20])[CH3:19]>>[CH2:17]([O:21][CH2:2][C:3]([CH3:16])=[CH:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1)[CH:18]([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 6560Isobutanol2×HCID 54512866HCID 54512866, compound

Product 1

HCID 54408087HCID 54408087, compound

Procedure

1.6 g (0.0165 mol) of sodium-isobutylate in 75 cc of isobutanol are added dropwise at 70° during the course of 15 minutes to 4.3 g (0.015 mol) of 5-(4-bromo-3-methyl-2-butenyloxy)-1,3-benzodioxol which is dissolved in 130 cc of isobutanol. After 3 hours at this temperature the reaction mixture is filtered, the solvent is distilled off at reduced pressure and the residue is dissolved in ether. The ether solution is washed with saturated salt solution, is dried with sodium sulphate and evaporated. The residue is chromatographed on silica gel with chloroform. 5-(4-isobutoxy-3-methyl-2-butenyloxy)-1,3-benzodioxol is obtained as colourless oil. nD20 = 1.5158.

Workup

  1. filtrationAfter 3 hours at this temperature the reaction mixture is filtered
  2. distillationthe solvent is distilled off at reduced pressure
  3. dissolutionthe residue is dissolved in ether
  4. washThe ether solution is washed with saturated salt solution
  5. dry with materialis dried with sodium sulphate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with chloroform

Sources & evidence

ORD record
ord-5a0ae836d9e94a14b6f454b58603c141
Source dataset
uspto-grants-1976_01
Patent number
US03933804

Reaction notes

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