1,4-Cyclohexanediol → t-Butyl (4-hydroxycyclohexyl)acetate

HRID 1682681노트

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HRID 1682681 반응식
[OH-].[Na+].[CH:3]1([OH:10])[CH2:8][CH2:7][CH:6](O)[CH2:5][CH2:4]1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:10][CH:3]1[CH2:4][CH2:5][CH:6]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:8]1

참가 물질

6

반응물 3

HCID 111621,4-CyclohexanediolHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetate

생성물 1

HCID 18919465t-Butyl (4-hydroxycyclohexyl)acetate수율 7.6%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

실험 절차

Sodium hydroxide (5.7 g, 0.14 mol) was dissolved in water (6 ml) and 1,4-cyclohexanediol (cis/trans=6/4) (15.0 g, 0.13 mol) was added, which was followed by stirring at room temperature for 30 minutes. Then, tetrabutylammonium bromide (20.8 g, 0.065 mol) and t-butyl bromoacetate (24.5 ml, 0.13 mol) were added, and the mixture was stirred at room temperature for one hour. The reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column Chromatography (n-hexane/ethyl acetate=5/1-2/1) to give 2.13 g of t-butyl (4-hydroxycyclohexyl)acetate as a transparent oil (7%).

후처리

  1. stirringthe mixture was stirred at room temperature for one hour
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration, low boiling matters
  5. distillationwere distilled away from the filtrate under reduced pressure
  6. customthe residue was purified by silica gel column Chromatography (n-hexane/ethyl acetate=5/1-2/1)

출처 및 근거

ORD 기록
ord-1d6df9dcd6f04743975233913c657566
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05635527

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