Acetone → 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

HRID 4107

반응식

HRID 4107 반응식
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.CC(C)=[O:20].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>O>[O:9]=[C:7]1[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][O:4][C:3]([C:2]([OH:20])=[O:1])=[CH:8]1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 131709961Jones' reagent

생성물 1

HCID 64807825-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid수율 5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

232 g (1 mol) of 2-(hydroxymethyl)-5-(phenylmethoxy)-4H-pyran-4-one was put into a 10 l stirring flask containing 6.6 l of acetone and 400 ml of water. The clear solution was cooled to +5° C. by means of an ice bath. While maintaining the temperature at +5° C. to 10° C., 640 ml of Jones reagent (202 g CrO3, 600 ml water, 174 ml H2SO4) was added dropwise over a period of 1 hour. Stirring was continued for 2 hours without cooling. The reaction mixture was filtered through a glass frit and the dark green residue washed with 500 ml of acetone. The filtrate was then evaporated until all of the acetone was removed. To the aqueous, partly crystalline product was added 1.2 l of methanol, and this mixture was then heated to its boiling point. The resulting clear dark green solution was placed in an ice bath and the product allowed to crystallize. The crystalline product was filtered and washed with 500 ml of a cold solvent mixture consisting of 250 ml of methanol +250 ml of water and finally dried. Yield: 195 g. From the mother liquor, a further 5% of the product could be isolated.

후처리

  1. temperatureThe clear solution was cooled to +5° C. by means of an ice bath
  2. temperatureWhile maintaining the temperature at +5° C. to 10° C.
  3. stirringStirring
  4. temperaturewithout cooling
  5. filtrationThe reaction mixture was filtered through a glass frit
  6. washthe dark green residue washed with 500 ml of acetone
  7. customThe filtrate was then evaporated until all of the acetone
  8. customwas removed
  9. additionTo the aqueous, partly crystalline product was added 1.2 l of methanol
  10. temperaturethis mixture was then heated to its boiling point
  11. customThe resulting clear dark green solution was placed in an ice bath
  12. customto crystallize
  13. filtrationThe crystalline product was filtered
  14. washwashed with 500 ml of a cold solvent mixture
  15. customfinally dried

출처 및 근거

ORD 기록
ord-4f60e5d4a7d141feb6cb2275775489e2
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723002

연결된 노트

불러오는 중…