Acetic Acid → CYANO-CYCLOHEXYLIDENE-ACETIC ACID METHYL ESTER

HRID 1297220ノート

反応式

HRID 1297220 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 11229121CYANO-CYCLOHEXYLIDENE-ACETIC ACID METHYL ESTER

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fee0b23fefec4e00a52385268654f8e5
出典データセット
uspto-grants-2007_07
特許番号
US07250433B2

反応ノート

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