Cyclohexanone Oxime → 3-[(Cyclohexylideneamino)oxy]propanoic acid

HRID 1450677ノート

反応式

HRID 1450677 の反応式
[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:13]CC)(=[O:12])[CH:10]=[CH2:11].[OH-].[K+]>C(O)C>[C:1]1(=[N:7][O:8][CH2:11][CH2:10][C:9]([OH:13])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 7517Cyclohexanone OximeHCID 8821Ethyl AcrylateHCID 14797Potassium Hydroxide

生成物 1

HCID 199772093-[(Cyclohexylideneamino)oxy]propanoic acid収率 24,503%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
60 °C

実験手順

A mixture of 32.8 g (0.29 mol) of cyclohexanone oxime, 26 g (0.26 mmol) of ethyl acrylate, 26 ml (0.052 mol) of a 2N solution of KOH in ethanol and 150 ml of ethanol is stirred for 96 hours at 60° C. and afterwards concentrated on a vacuum rotary evaporator. The residue (an orange oil) is dissolved in 175 g (0.31 tool) of a 10% solution of KOH in ethanol and the solution is heated for 1 hour to 60° C. The solvent is distilled off and the solid residue is taken up in water. After acidification with c. 15 ml of conc. hydrochloric acid and extraction with ethyl acetate, the organic phase is washed with water, dried over Na2SO4 and concentrated on a vacuum rotary evaporator. Distillation of the residue yields 11.8 g (25%) of the desired acid as an orange liquid. The boiling point is 135° C./0.05 mbar.

後処理

  1. concentrationafterwards concentrated on a vacuum rotary evaporator
  2. dissolutionThe residue (an orange oil) is dissolved in 175 g (0.31 tool) of a 10% solution of KOH in ethanol
  3. temperaturethe solution is heated for 1 hour to 60° C
  4. distillationThe solvent is distilled off
  5. extraction15 ml of conc. hydrochloric acid and extraction with ethyl acetate
  6. washthe organic phase is washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated on a vacuum rotary evaporator
  9. distillationDistillation of the residue

出典と根拠

ORDレコード
ord-2f76d6ee00514261b05b6fa40148cab8
出典データセット
uspto-grants-1997_02
特許番号
US05602196

反応ノート

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