m-Chloroperbenzoic acid → HCID 54018462, compound

HRID 1388128Notes

Reaction equation

HRID 1388128 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5](=[CH2:15])[CH2:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]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][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:15][O:25]1)=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54419238HCID 54419238, compound

Product 1

HCID 54018462HCID 54018462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

7.9 g of 5-cyclohexyl-2-methylenevaleric acid ethyl ester and 12.2 g of m-chloroperbenzoic acid in 100 ml of methylene chloride are boiled under reflux for 21 hours. The mixture is cooled to 0° C., the precipitate is filtered off and washed with 50 ml of methylene chloride and the combined filtrates are concentrated. The turbid, oily residue is dissolved in 60 ml of acetone and dilute sodium carbonate solution is added, while cooling with ice, until a pH value of 9 is reached. 100 ml of water are also added and the mixture is extracted with 3 times 100 ml of diethyl ether. The combined organic phases are dried over sodium sulphate and concentrated and the oily residue is distilled. This gives 4.9 g of the title compound, bp 100°-108° C. at 0.02 mm Hg (2.7 Pa).

Workup

  1. temperatureunder reflux for 21 hours
  2. filtrationthe precipitate is filtered off
  3. washwashed with 50 ml of methylene chloride
  4. concentrationthe combined filtrates are concentrated
  5. dissolutionThe turbid, oily residue is dissolved in 60 ml of acetone
  6. additiondilute sodium carbonate solution is added
  7. temperaturewhile cooling with ice, until a pH value of 9
  8. addition100 ml of water are also added
  9. extractionthe mixture is extracted with 3 times 100 ml of diethyl ether
  10. dry with materialThe combined organic phases are dried over sodium sulphate
  11. concentrationconcentrated
  12. distillationthe oily residue is distilled

Sources & evidence

ORD record
ord-e080ace844a04d6d90864fb69f31a7a7
Source dataset
uspto-grants-1984_02
Patent number
US04430339

Reaction notes

Loading…