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

HRID 230919

反応式

HRID 230919 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 80803,4-dihydro-2H-pyran溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1df02b8e5f4241548e4ca6542d9a9fd7
出典データセット
uspto-grants-2009_07
特許番号
US07566699B2

関連ノート

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