Sodium hydride → Dimethyl 2-(2,4,5-trimethylphenyl)-malonate

HRID 1872657ノート

反応式

HRID 1872657 の反応式
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH3:11])=[CH:6][C:5]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14]>C(=O)(OC)OC>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH3:11])=[CH:6][C:5]=1[CH:12]([C:13]([O:15][CH3:16])=[O:14])[C:13]([O:15][CH3:16])=[O:14]

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 22336857Methyl 2,4,5-trimethylphenylacetate

生成物 1

HCID 22336858Dimethyl 2-(2,4,5-trimethylphenyl)-malonate収率 164.9%

試薬・触媒・溶媒 1

HCID 12021Dimethyl Carbonate溶媒2 回

反応条件

温度
80 °C

実験手順

18.6 g (0.62 mol, 80% pure) of sodium hydride were initially introduced into 384 ml of dimethyl carbonate and the mixture was heated to about 80° C. 48 g (0.25 mol) of methyl 2,4,5-trimethylphenylacetate, dissolved in 100 ml of dimethyl carbonate, were then added dropwise and the mixture was heated under reflux for 4 hours. It was cooled to room temperature, the excess sodium hydride was destroyed with ethanol and the mixture was then poured into 1500 ml of ice-water. A pH of 4 to 5 was established with 6 N hydrochloric acid and the organic phase was taken up in toluene. The organic phase was separated off, dried and concentrated and the residue was employed in the next stage without further purification. 51.6 g of dimethyl 2-(2,4,5-trimethylphenyl)-malonate were obtained as an oil.

後処理

  1. additionwere then added dropwise
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. temperatureIt was cooled to room temperature
  5. customthe excess sodium hydride was destroyed with ethanol
  6. additionthe mixture was then poured into 1500 ml of ice-water
  7. customThe organic phase was separated off
  8. customdried
  9. concentrationconcentrated
  10. customthe residue was employed in the next stage without further purification

出典と根拠

ORDレコード
ord-4a3adb6f9b4f4e9ca564b9689a5455b8
出典データセット
uspto-grants-2000_08
特許番号
US06110872

反応ノート

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