Dimethyl Sulfoxide → (1-Nitromethylcyclohexyl)acetic acid ethyl ester

HRID 1535027노트

반응식

HRID 1535027 반응식
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(=O)([O-])[O:9][CH2:10][CH3:11].[OH-].[K+].[N+:16]([CH3:19])([O-:18])=[O:17].[C:20](=[O:23])([O-])[O-].[K+].[K+].[CH3:26]S(C)=O>CCCCCC.O>[N+:16]([CH2:19][C:1]1([CH2:11][C:10]([O:23][CH2:20][CH3:26])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:18])=[O:17]

참가 물질

9

반응물 6

HCID 679Dimethyl Sulfoxide2회HCID 6375NitromethaneHCID 7967CyclohexanoneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 178476831HCID 178476831, 화합물

생성물 1

HCID 11128083(1-Nitromethylcyclohexyl)acetic acid ethyl ester수율 83%

시약·촉매·용매 2

HCID 962Water용매HCID 8058Hexane용매

실험 절차

98.15 g (1.00 mole) Cyclohexanone are mixed with 35.4 g (1.05 mole) ethyl phosphonate and mixed at 25° to 30° C. with 66.1 g (1.04 mole) potassium hydroxide powder (content 88%). The reaction mixture is further stirred for 30 minutes and successively mixed with 150 mL dimethyl sulphoxide and 86.0 g (1.41 mole) nitromethane. This solution is added dropwise at 110° to 115° C. over 35 minutes to a suspension of 64.7 g (0.47 mole) potassium carbonate in 470 mL dimethyl sulphoxide. Then stirring is continued for 2 to 3 hours and the reaction mixture is mixed with water and subsequently extracted several times with n-hexane. The combined organic phases are washed with water, dried over anhydrous sodium sulphate and the solvent then distilled off in a vacuum. 191.5 g ethyl 1-nitromethyl-1-cyclohexaneacetate in the form of an oil are obtained (yield 83% of theory). Composition according to HPLC: 88.7% of the product of Step 2 and 6.3% of the product of Step 1.

후처리

  1. stirringThen stirring
  2. waitis continued for 2 to 3 hours
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. distillationthe solvent then distilled off in a vacuum

출처 및 근거

ORD 기록
ord-2e738ade350a4467bbb0afbface59801
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05091567

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