m-Chloroperbenzoic acid → HCID 12932109, compound

HRID 2285740Notes

Reaction equation

HRID 2285740 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5](=[CH2:15])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:15][O:25]1)=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10489014HCID 10489014, compound

Product 1

HCID 12932109HCID 12932109, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

10 g of 5-phenyl-2-methylenevaleric acid ethyl ester and 18.3 g of m-chloroperbenzoic acid (85% pure) are boiled under reflux in 180 ml of methylene chloride for 40 hours. The mixture is allowed to cool; the m-chloroperbenzoic acid (which has separated out) is filtered off; the filtrate is concentrated; the residue is taken up in 40 ml of acetone; 20 ml of a saturated sodium carbonate solution are added, and the mixture is stirred at 0° C. for 1 hour. It is then diluted with 100 ml of water and extracted 3 times with 50 ml of methylene chloride each time; the organic phase is concentrated, and the residue is distilled. 8.3 g of the liquid title compound (b.p. 115° under 0.03 mm Hg) are obtained.

Workup

  1. temperatureto cool
  2. customthe m-chloroperbenzoic acid (which has separated out)
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated
  5. addition20 ml of a saturated sodium carbonate solution are added
  6. additionIt is then diluted with 100 ml of water
  7. extractionextracted 3 times with 50 ml of methylene chloride each time
  8. concentrationthe organic phase is concentrated
  9. distillationthe residue is distilled

Sources & evidence

ORD record
ord-90c95ff8654d4f73bf637d7523174807
Source dataset
uspto-grants-1982_04
Patent number
US04324796

Reaction notes

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