Sulfuric Acid → 2H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

HRID 263924

반응식

HRID 263924 반응식
S(=O)(=O)(O)O.[CH:6](OC)(OC)OC.[CH3:13][C:14]1[C:15]([OH:23])=[C:16]([CH3:22])[C:17]([CH3:21])=[C:18]([CH:20]=1)[OH:19].[CH:24]([C:26]([CH3:28])=[O:27])=[CH2:25]>CO.C(OCC)C>[OH:23][C:15]1[C:14]([CH3:13])=[C:20]2[C:18](=[C:17]([CH3:21])[C:16]=1[CH3:22])[O:19][C:26]([O:27][CH3:6])([CH3:28])[CH2:24][CH2:25]2

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketoneHCID 9005Trimethyl orthoformateHCID 12785Trimethylhydroquinone

생성물 1

HCID 1037632H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-수율 92.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

Concentrated sulfuric acid (0.8 mL) was added dropwise to a solution of trimethyl orthoformate (Aldrich, 48.5 g, 457.0 mmol) and trimethyl hydroquinone (Aldrich, 50.0 g, 328.5 mol) in methanol (200 mL), cooled by a water/ice bath. Methyl vinyl ketone (Aldrich, 46.05 g, 657.0 mmol) was added slowly (1.5 h) to the reaction mixture while the reaction mixture was cooled by an ice/water bath. A pasty slurry formed. The reaction mixture was allowed to come to ambient temperature and was stirred at ambient temperature for 48 h. The reaction mixture was diluted with diethyl ether (600 mL) and the resulting solution was extracted with water (2×200 mL) and saturated aqueous sodium bicarbonate (2×100 mL). The organic solution was dried (sodium sulfate) and concentrated in vacuo to give a tan solid. The solid was recrystallized from methanol to give 71.8 g (92.6%) of the desired product as a tan solid.

후처리

  1. temperaturecooled by a water/ice bath
  2. temperaturewas cooled by an ice/water bath
  3. customA pasty slurry formed
  4. customto come to ambient temperature
  5. extractionthe resulting solution was extracted with water (2×200 mL) and saturated aqueous sodium bicarbonate (2×100 mL)
  6. dry with materialThe organic solution was dried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto give a tan solid
  9. customThe solid was recrystallized from methanol

출처 및 근거

ORD 기록
ord-e869cbf248364ce393243da6e7bfa8b3
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646149

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