Benzyl Alcohol → 4-Benzyloxy-3-pyrrolin-2-one

HRID 1722471

반응식

HRID 1722471 반응식
[CH3:1][O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1.C(O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 5747694-methoxy-2,5-dihydro-1H-pyrrol-2-one

생성물 1

HCID 27247414-Benzyloxy-3-pyrrolin-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

5.7 g (50 mmol) of 4-methoxy-3-pyrrolin-2-one and 10.8 g (100 mmol) of benzyl alcohol were mixed with 0.4 g (4 mmol) of methanesulfonic acid and stirred for 24 hours at 80° C. and 20 mbars. Then the reaction solution was mixed with 50 ml of ice water and 100 ml of methylene chloride, and neutralized with 4 ml of saturated NaHCO3 solution. The aqueous phase was extracted twice with 50 ml of methylene chloride each. After drying of the organic phase over Na2SO4 and distilling off of the solvent, the residue was mixed with 150 ml of ice water, heated to 100° C. and azeotropically distilled off with 100 ml of water-benzyl alcohol. The crystals precipitated during cooling were recrystallized hot from 50 ml of toluene. 6.7 g of white, crystalline product with a melting point of 147° to 148° C. was obtained:

후처리

  1. extractionThe aqueous phase was extracted twice with 50 ml of methylene chloride each
  2. dry with materialAfter drying of the organic phase over Na2SO4
  3. distillationdistilling off of the solvent
  4. additionthe residue was mixed with 150 ml of ice water
  5. temperatureheated to 100° C.
  6. distillationazeotropically distilled off with 100 ml of water-benzyl alcohol
  7. customThe crystals precipitated
  8. temperatureduring cooling
  9. customwere recrystallized hot from 50 ml of toluene
  10. custom6.7 g of white, crystalline product with a melting point of 147° to 148° C. was obtained

출처 및 근거

ORD 기록
ord-04e440d11a534283a9a851cb36ad1d00
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04855451

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