m-Chloroperbenzoic acid → HCID 22749297, compound

HRID 1076747Notes

Reaction equation

HRID 1076747 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)Cl>[O:26]1[C:2]([CH3:17])([CH3:1])[CH:3]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22749289HCID 22749289, compound

Product 1

HCID 22749297HCID 22749297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.15 g of p-[(3-methyl-2-butenyl)oxy]-α-propargyloxy-toluene is dissolved in 40 ml of methylene chloride and cooled to 0°C. (ice-bath cooling). 1.5 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 p-[(2,3-epoxy-3-methylbutyl)oxy]-α-propargyloxy-toluene; B.P. 120°-123°C/0.1 mmHg.

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-eb865e17fc2d4bc2aa5f8e08f3ed2112
Source dataset
uspto-grants-1976_05
Patent number
US03957833

Reaction notes

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