2',6'-Dihydroxyacetophenone → 6'-Hydroxy-2'-(tetrahydropyran-2-yloxy)acetophenone

HRID 230919

반응식

HRID 230919 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10].[OH2:12].[C:13]1(C)C=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1>O1CCOCC1.O1C=CCCC1.C(OCC)C>[OH:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[C:4]([O:8][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 2

HCID 696872',6'-DihydroxyacetophenoneHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 113567996'-Hydroxy-2'-(tetrahydropyran-2-yloxy)acetophenone수율 2,162.3%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 80803,4-dihydro-2H-pyran용매HCID 312751,4-Dioxane용매

실험 절차

2′,6′-Dihydroxyacetophenone (5.0 g) was dissolved in dioxane (20 mL) and 3,4-dihydro-2H-pyran (16 mL). To the solution was added p-toluenesulfonic acid monohydrate (0.21 g), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with diethyl ether, and the mixture was washed with 5% aqueous potassium carbonate solution. The organic layer was extracted with 2 mol/L aqueous sodium hydroxide solution, and the aqueous layer was neutralized until pH was about 8. The resulting mixture was extracted with diethyl ether. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate to give the title compound (5.64 g).

후처리

  1. washthe mixture was washed with 5% aqueous potassium carbonate solution
  2. extractionThe organic layer was extracted with 2 mol/L aqueous sodium hydroxide solution
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate

출처 및 근거

ORD 기록
ord-1df02b8e5f4241548e4ca6542d9a9fd7
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566699B2

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