Water → Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate

HRID 1796357노트

반응식

HRID 1796357 반응식
[Cl:1][CH2:2][CH:3]([OH:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.O>CC(C)=O.C(O)(C)C>[Cl:1][CH2:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:17])([CH3:18])[C:13]([O:15][CH3:16])=[O:14]

참가 물질

7

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21866631Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionateHCID 131709961Jones' reagent2회

생성물 1

HCID 21866630Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate수율 59%

시약·촉매·용매 2

HCID 180Acetone용매HCID 3776Isopropanol용매

실험 절차

Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionate (31 g) was dissolved in 465 ml of acetone, and 46 ml of Jones reagent prepared by adding 10.2 ml of conc. sulfuric acid and 12 g of chromic (VI) oxide to 45 ml of water was added dropwise with stirring under ice-cooling. After 3-hour-stirring at room temperature, an excess amount of Jones reagent was decomposed by adding isopropyl alcohol, The reaction mixture was poured into ice-cold water, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=7.5:1) to provide 18.16 g of the objective compound as oil.

후처리

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringAfter 3-hour-stirring at room temperature
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=7.5:1)

출처 및 근거

ORD 기록
ord-938d90b548a747d982b34cb63b9bd352
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030143B2

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