m-Chloroperbenzoic acid → HCID 11137981, compound

HRID 1904410Notes

Reaction equation

HRID 1904410 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])=[CH:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:19]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][O:19]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 133952001-Methoxy-4-(pent-4-en-1-yl)benzene

Product 1

HCID 11137981HCID 11137981, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(4-Methoxyphenyl)pent-1-ene (18.9 g, 0.107 mol) and 3-chloroperoxybenzoic acid (22.3 g of 85%, 0.11 mol) in dichloromethane (250 ml) was stirred at room temperature for 25 minutes. Dichloromethane (150 ml) was added and the resulting solution was washed with saturated aqueous sodium hydrogen carbonate solution (3×300 ml) and dried (MgSO4). The solvent was evaporated off under reduced pressure to yield an oil which was purified by column chromatography (silica gel, chloroform) to yield [3-(4-methoxyphenyl)propyl]oxirane as a colourless oil having the following structural characteristics:

Workup

  1. washthe resulting solution was washed with saturated aqueous sodium hydrogen carbonate solution (3×300 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated off under reduced pressure
  4. customto yield an oil which
  5. customwas purified by column chromatography (silica gel, chloroform)

Sources & evidence

ORD record
ord-ff8e7468767b4e918d53b36d764bdda1
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

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