m-Chloroperbenzoic acid → HCID 86755926, compound

HRID 366284Notes

Reaction equation

HRID 366284 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH3:8].ClC1C=CC=C(C(OO)=[O:17])C=1>ClCCl>[CH2:7]([C@H:6]1[C@@H:5]([CH2:4][CH2:3][O:2][CH3:1])[O:17]1)[CH3:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5364230(3Z)-1-Methoxy-3-hexene

Product 1

HCID 86755926HCID 86755926, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

27.4 g of (Z)-1-methoxy-3-hexene were dissolved in dichloromethane (850 ml) and cooled to 10°. 62 g of ca 70% m-chloroperbenzoic acid corresponding to 1.05 eq., were added in portions. The mixture was allowed to react during 15 hours and was then transferred into an extraction funnel wherein it was washed with an aqueous solution of NaOH and then with water to neutrality. After separation and drying of the organic layer on Na2SO4, the residue was distilled over a 5 cm long Vigreux type column at 51-52°/1.5×103Pa to give 24.9 g (80%) of the desired compound in the form of a colourless liquid which presented the following analytical data:

Workup

  1. temperaturecooled to 10°
  2. customto react during 15 hours
  3. customwas then transferred into an extraction funnel
  4. washwherein it was washed with an aqueous solution of NaOH
  5. customAfter separation
  6. customdrying of the organic layer on Na2SO4
  7. distillationthe residue was distilled over a 5 cm long Vigreux type column at 51-52°/1.5×103Pa

Sources & evidence

ORD record
ord-338e58e77cd24c89b0a9bce6c69402b7
Source dataset
uspto-grants-2000_10
Patent number
US06129941

Reaction notes

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