m-Chloroperbenzoic acid → HCID 22749281, compound

HRID 1390398Notes

Reaction equation

HRID 1390398 reaction equation
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[CH:15])=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[O:25]1[C:2]([CH3:16])([CH3:1])[CH:3]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][C:14]#[CH:15])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22749282HCID 22749282, compound

Product 1

HCID 22749281HCID 22749281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6.4 g of 1-[(3-methyl-2-butenyl)oxy]-4-propargyloxy-benzene is dissolved in 80 ml of methylenechloride and cooled to 0° C. (ice-bath cooling). 7.15 g of 80% by weight m-chloroperbenzoic acid is added portionwise to this mixture and the solution is thereafter stirred at 0° C. for 2 hours. The mixture is worked up as follows: diluted with 350 ml of methylene chloride; washed with ice-cold 1-N caustic soda; washed with saturated aqueous sodium chloride solution; dried over sodium sulfate; and evaporated. By chromatography on Kieselgel, there is obtained 1-[(2,3-epoxy-3-methylbutyl)oxy]-4-propargyloxy-benzene; M.P. 72°-73° C.

Workup

  1. temperature(ice-bath cooling)
  2. washwashed with ice-cold 1-N caustic soda
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customand evaporated

Sources & evidence

ORD record
ord-b3c2e80c59bf48659912beac1ea0c36a
Source dataset
uspto-grants-1979_02
Patent number
US04138579

Reaction notes

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