Acetone → HCID 71278892, 화합물

HRID 1749719노트

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HRID 1749719 반응식
O[C:2]1C(C)=[CH:9][C:8]([OH:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.S([O:18][CH3:19])(OC)(=O)=O.[C:20](=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].[CH3:32][C:33](C)=[O:34]>>[CH3:20][O:12][C:8]1[CH:7]=[C:3]([CH3:2])[C:4]([O:6][CH2:32][C:33]([O:18][CH3:19])=[O:34])=[C:27]([CH:9]=1)[C:28]([O:30][CH3:31])=[O:29]

참가 물질

6

반응물 5

HCID 180Acetone2회HCID 6497Dimethyl SulfateHCID 11430Potassium Carbonate2회HCID 60984Methyl bromoacetateHCID 144020332,5-Dihydroxy-3-methylbenzoic acid

생성물 1

HCID 71278892HCID 71278892, 화합물수율 63%

실험 절차

2,5-Dihydroxy-3-methylbenzoic acid (4.7 g, 29 mmol) was added successively with acetone (40 mL), dimethyl sulfate (9.0 g, 71 mmol), and potassium carbonate (10 g, 72 mmol), and the mixture was stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure, the residue was added with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was successively added with acetone (50 mL), potassium carbonate (1.0 g, 72 mmol), and methyl bromoacetate (6.6 g, 43 mmol), and then the mixture was refluxed for 8 hours by heating. The reaction mixture was filtered through Celite, and then the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (70:30→50:50)) to obtain methyl 5-methoxy-2-(2-methoxy-2-oxoethoxy)-3-methylbenzoate (4.9 g, 63%).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with ethyl acetate
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. temperaturethe mixture was refluxed for 8 hours
  7. temperatureby heating
  8. filtrationThe reaction mixture was filtered through Celite
  9. customthe solvent was evaporated under reduced pressure
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. washthe organic layer was washed successively with water and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (70:30→50:50))

출처 및 근거

ORD 기록
ord-a59c6d46701d409aa99501e3d45fd110
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156827B2

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