Acetic Acid → CYANO-CYCLOHEXYLIDENE-ACETIC ACID METHYL ESTER

HRID 1297220노트

반응식

HRID 1297220 반응식
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])#[N:9].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1>[CH3:14][O:13][C:11](=[O:12])[C:10]([C:8]#[N:9])=[C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7747Methyl cyanoacetateHCID 7967CyclohexanoneHCID 517165Ammonium Acetate

생성물 1

HCID 11229121CYANO-CYCLOHEXYLIDENE-ACETIC ACID METHYL ESTER

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a solution of cyclohexanone (84.1 g, 1 mol) in dry benzene (100 mL) was added methyl cyanoacetate (99.1 g, 1 mol), ammonium acetate (10 g) and glacial acetic acid (20 mL). The reaction mixture was heated to reflux using Dean-Stark apparatus for 12 hours and allowed to cool to room temperature. Excess of solvents was removed in vacuo and the residue was dissolved in EtOAc (400 mL). The organic layer was washed with water, dried over sodium sulfate and evaporated to give cyano-cyclohexylidene-acetic acid methyl ester as pale yellow oil. Further purification of the pale yellow oil by distillation (10 mm Hg, 150-155° C.) gave product 15 (110 g, 61%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 1.70-1.85 (m, 6H), 2.70 (t, 2H), 3.00 (t, 2H), 3.80 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 25.9, 28.6, 28.9, 31.9, 37.2, 52.8, 101.9, 115.8, 162.7, 180.8.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customfor 12 hours
  4. customExcess of solvents was removed in vacuo
  5. dissolutionthe residue was dissolved in EtOAc (400 mL)
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated

출처 및 근거

ORD 기록
ord-fee0b23fefec4e00a52385268654f8e5
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250433B2

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