Sodium Sulfite → (7-Oxabicyclo(4.1.0)heptan-3-yl)methyl 2-methylprop-2-enoate

HRID 1728366노트

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HRID 1728366 반응식
[C:1]([O:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].ClC1C=CC=C(C(OO)=[O:22])C=1.S([O-])([O-])=O.[Na+].[Na+].C1C(C(O[O-])=O)=CC=CC=1>C(Cl)Cl>[C:1]([O:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH:11]2[O:22][CH:10]2[CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

참가 물질

6

반응물 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 14473552Cyclohexen-4-ylmethyl methacrylateHCID 15871866Perbenzoate2회

생성물 1

HCID 14645478(7-Oxabicyclo(4.1.0)heptan-3-yl)methyl 2-methylprop-2-enoate수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A 8 liter, 4 necked flask equipped with a thermometer, cooling jacket, stirring means and drip funnel was charged with 200 g of cyclohexen-4-ylmethyl methacrylate produced in Step A and 1200 ml of methylene chloride. The reactants were cooled to a temperature below 10° C. A solution of 268.6 g of m-chloroperbenzoic acid (80% purity, Kishida Chemicals) in 2800 ml of methylene chloride was added thereto dropwise over 3 hours and then allowed to react for additional 3 hours with stirring. After the reaction, an amount of 10% aqueous solution of sodium sulfite was added to the reaction mixture and allowed to react at room temperature for 1 hour to decompose unreacted perbenzoate. After having confirmed the absence of perbenzoate using starch-iodine indicator paper, the reaction mixture was washed with 1000 ml of an aqueous solution containing 81 g of sodium carbonate and then with an amount of saline successively. Thereafter the mixture was dried over magnesium sulfate and evaporated under reduced pressure with addition of 40 mg of p-methoxyquinone as a polymerization inhibitor to remove the solvent. 206 g of crude product of the titled compound was obtained. Yield: 95% of theory.

후처리

  1. customA 8 liter, 4 necked flask equipped with a thermometer
  2. temperaturecooling jacket
  3. temperatureThe reactants were cooled to a temperature below 10° C
  4. customto react for additional 3 hours
  5. stirringwith stirring
  6. customAfter the reaction
  7. customto react at room temperature for 1 hour
  8. washthe reaction mixture was washed with 1000 ml of an aqueous solution
  9. additioncontaining 81 g of sodium carbonate
  10. dry with materialThereafter the mixture was dried over magnesium sulfate
  11. customevaporated under reduced pressure with addition of 40 mg of p-methoxyquinone as a polymerization inhibitor
  12. customto remove the solvent

출처 및 근거

ORD 기록
ord-f44f18d6614c427eabf63ae1bdcd270b
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05326827

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