m-Chloroperbenzoic acid → HCID 53772934, compound

HRID 1577000Notes

Reaction equation

HRID 1577000 reaction equation
[CH3:1][C:2]([CH2:15][CH2:16][C:17]([CH3:21])=[C:18]([CH3:20])[CH3:19])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[O:30]1[C:18]([CH3:20])([CH3:19])[C:17]1([CH3:21])[CH2:16][CH2:15][C:2]([CH3:1])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54307017HCID 54307017, compound

Product 1

HCID 53772934HCID 53772934, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution containing 10.4 g. of 3,6,7-trimethyl-1-[3,4-(methylenedioxy)-phenoxy]-2,6-octadiene in 100 ml. of methylenechloride, 7 g. of m-chloroperbenzoic acid were added portionwise. After this addition, the reaction mixture was allowed to stand for 2 hours at 0° to 3°C. under constant stirring. After this period, the reaction mixture was diluted with 250 ml. of diethylether, and washed with ice cold 1N sodium hydroxide and saturated aqueous sodium chloride solution. After washing, the reaction mixture was dried over sodium sulfate and evaporated. By chromatography on Kieselgel with hexane-diethylether (4:1 parts by volume) and distillation under vcuum, there was obtained pure 6,7-epoxy-3,6,7-trimethyl-1-[3,4-(methylenedioxy)-phenoxy]-2-octene; b.p. 120°-122°C./0.004 mmHg; nD20 = 1.5277.

Workup

  1. additionAfter this addition
  2. waitAfter this period
  3. additionthe reaction mixture was diluted with 250 ml
  4. washof diethylether, and washed with ice cold 1N sodium hydroxide and saturated aqueous sodium chloride solution
  5. washAfter washing
  6. dry with materialthe reaction mixture was dried over sodium sulfate
  7. customevaporated
  8. distillationBy chromatography on Kieselgel with hexane-diethylether (4:1 parts by volume) and distillation under vcuum

Sources & evidence

ORD record
ord-81d88de5c7914cd29bbc3526af814616
Source dataset
uspto-grants-1976_09
Patent number
US03983243

Reaction notes

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