m-Chloroperbenzoic acid → HCID 53784409, compound

HRID 596640Notes

Reaction equation

HRID 596640 reaction equation
[CH2:1]1[O:23][C:4]2[CH:5]=[C:6]([O:9][CH2:10][CH:11]=[C:12]([CH3:22])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:21])[CH2:17][CH:18]([CH3:20])[CH3:19])[CH:7]=[CH:8][C:3]=2[O:2]1.ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl>[O:32]1[C:16]([CH3:21])([CH2:17][CH:18]([CH3:19])[CH3:20])[CH:15]1[CH2:14][CH2:13][C:12]([CH3:22])=[CH:11][CH2:10][O:9][C:6]1[CH:7]=[CH:8][C:3]2[O:2][CH2:1][O:23][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53894984HCID 53894984, compound

Product 1

HCID 53784409HCID 53784409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 10 g. of 1,2-(methylenedioxy)-4-[(3,7,9-trimethyl-2,6-decadienyl)oxy]-benzene dissolved in 100 ml. of methylene chloride are added portionwise, while stirring and cooling with ice at 1°-5° C., 6.85 g. of 80% m-chloroperbenzoic acid and the mixture is stirred for a further 2 hours while cooling with ice. The mixture is subsequently diluted with 200 ml. of ether and washed successively with ice-cold 1-N aqueous sodium hydroxide, water and saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated. By chromatography on silica gel with hexane/ether (4:1 parts by volume), there is obtained pure 4-[(6,7-epoxy-3,7,9-trimethyl-2-decenyl)-oxy]-1,2-(methylenedioxy)-benzene of boiling point (bulb tube) 135°-140° C./0.02 mm Hg.; nD22 = 1.5168.

Workup

  1. temperaturecooling with ice at 1°-5° C.
  2. temperaturewhile cooling with ice
  3. additionThe mixture is subsequently diluted with 200 ml
  4. washof ether and washed successively with ice-cold 1-N aqueous sodium hydroxide, water and saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-3af3f7ea6d4043abafd0629d52b21a8c
Source dataset
uspto-grants-1977_03
Patent number
US04011335

Reaction notes

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