Iodine → (1-Hydroxy-cyclohexyl)-acetic acid ethyl ester

HRID 735746

반응식

HRID 735746 반응식
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>C1COCC1.[Zn]>[OH:7][C:1]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 7967Cyclohexanone

생성물 1

HCID 219250(1-Hydroxy-cyclohexyl)-acetic acid ethyl ester수율 95.2%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of cyclohexanone (9.52 g, 97.0 mmol), a zinc powder (7.6 g, 116.4 mmol) and a small amount of iodine in THF (100 ml) was added dropwise ethyl bromoacetate (11.8 ml, 106.7 mmol) under a nitrogen atmosphere, and the mixture was heated under reflux for 5 hrs. 10% Sulfuric acid (100 ml) was carefully added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound (17.2 g, 94%) as a colorless oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8bcfc1bdaf264e648bd3110d3b137544
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592453B2

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