Water → 4-Cyclododecylbutanoic acid

HRID 129534

반응식

HRID 129534 반응식
[OH2:1].C(#N)C.[C:5]1([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)C=CC=CC=1.I([O-])(=O)(=O)=[O:27].[Na+]>ClCCl.O.[Ru](Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[CH:14]1([CH2:13][CH2:12][CH2:11][C:5]([OH:27])=[O:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

8

반응물 4

HCID 962WaterHCID 6342AcetonitrileHCID 152966211-(3-Phenylpropyl)cyclododecaneHCID 23667635Sodium periodate

생성물 1

HCID 152966224-Cyclododecylbutanoic acid

시약·촉매·용매 3

HCID 6093376Ruthenium trichloride hydrate촉매HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

To a flask containing 90 mL of water, 60 mL of acetonitrile and 60 mL of carbon tetrachloride is added 4.8 g (16.8 mmol) of 1-(3-phenylpropyl)cyclododecane, 50.0 g (0.25 mol) of sodium periodate and then 70 mg (0.3 mmol) of ruthenium trichloride hydrate. The reaction mixture is allowed to stir at room temperature overnight. The mixture is then taken up in dichloromethane and 1N HCl and the layers separated. The aqueous phase is washed 3 times with dichloromethane and the combined organic layers are dried over MgSO4 and the solvents evaporated. The residue is taken up in ether, filtered through Celite and the filtrate evaporated. The crude product is flash chromatographed using acidic silica gel and 30% ethyl acetate/hexanes to give 3.25 g of a white solid: NMR (CDCl3) δ 1.2-1.5 (m, 10H), 1.65 (m, 2H), 2.35 (t, 2H, J=8 Hz).

후처리

  1. custom1N HCl and the layers separated
  2. washThe aqueous phase is washed 3 times with dichloromethane
  3. dry with materialthe combined organic layers are dried over MgSO4
  4. customthe solvents evaporated
  5. filtrationfiltered through Celite
  6. customthe filtrate evaporated
  7. customchromatographed

출처 및 근거

ORD 기록
ord-541a3bc9d72a4776b6ae20a30a76a73f
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468774

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