m-Chloroperbenzoic acid → 6-[(6,7-Epoxy-3,7-dimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran

HRID 1414811Notes

Reaction equation

HRID 1414811 reaction equation
[CH3:1][C:2]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]2[CH2:10][CH2:11][O:12][C:8]=2[CH:7]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[O:29]1[C:18]([CH3:20])([CH3:19])[CH:17]1[CH2:16][CH2:15][C:2]([CH3:1])=[CH:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]2[CH2:10][CH2:11][O:12][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 541798386-[(3,7-Dimethylocta-2,6-dien-1-YL)oxy]-2,3-dihydro-1-benzofuran

Product 1

HCID 537513846-[(6,7-Epoxy-3,7-dimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18 g. of 6-[(3,7-dimethyl-2,6-octadienyl)-oxy]-2,3-dihydrobenzofuran are dissolved in 180 ml. of methylene chloride and, with stirring and ice cooling at 0°-5° C., 14.3 g. of 80% m-chloroperbenzoic acid are added portionwise. The mixture is then stirred for a further 2 hours with ice cooling. The mixture is subsequently diluted with 360 ml. of diethyl ether and washed successively with ice-cold 1-N aqueous sodium hydroxide and water. The organic phase is dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/diethyl ether (7:3 parts by volume) there is obtained pure 6-[(6,7-epoxy-3,7-dimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran of boiling point ca. 150° C./0.001 mmHg; nD20 = 1.5346.

Workup

  1. customat 0°-5° C.
  2. additionThe mixture is subsequently diluted with 360 ml
  3. washof diethyl ether and washed successively with ice-cold 1-N aqueous sodium hydroxide and water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a20ebf84fa71452d8cd6261e99e2e898
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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