Methyl iodide → 1-Chloro-4-hydroxy-4-methylnonane

HRID 258599

반응식

HRID 258599 반응식
I[CH3:2].[Mg].[Cl:4][CH2:5][CH2:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CCOCC>[Cl:4][CH2:5][CH2:6][CH2:7][C:8]([OH:14])([CH3:2])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 203861031-Chlorononan-4-one

생성물 1

HCID 203276741-Chloro-4-hydroxy-4-methylnonane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

The Grignard reagent prepared from iodomethane (14.2 g., 0.1 mole) and magnesium (2.4 g., 0.1 mole) in ether solution is added, dropwise to an ether solution of 1-chloro-4-nonanone (Example A, Step 1) (17.6 g., 0.1 mole). The reaction is refluxed gently for three hours then cooled and poured carefully into ice water (300 ml.). The ether layer is separated, washed with brine, and dried over sodium sulfate. Removal of the ether in vacuo gives 1-chloro-4-hydroxy-4-methylnonane as an oil. The tertiary alcohol is dissolved in pyridine and treated with one molar equivalent of acetic anhydride at 60°-80° for 8-16 hours to give 1-chloro-4-acetoxy-4-methylnonane as a colorless oil.

후처리

  1. temperatureThe reaction is refluxed gently for three hours
  2. temperaturethen cooled
  3. customThe ether layer is separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the ether in vacuo

출처 및 근거

ORD 기록
ord-a5dab223aef145f7ac998714dbc33b97
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04033996

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