Acetic Acid → 4-Hydroxy-3-methoxyphenylacetonitrile

HRID 1576875

反応式

HRID 1576875 の反応式
CN[CH2:3][C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.[C-:13]#[N:14].[Na+].C(O)(=O)C>CS(C)=O.O>[OH:10][C:9]1[CH:11]=[CH:12][C:4]([CH2:3][C:13]#[N:14])=[CH:5][C:6]=1[O:7][CH3:8]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 70607242-Methoxy-4-((methylamino)methyl)phenol

生成物 1

HCID 782204-Hydroxy-3-methoxyphenylacetonitrile

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
125 °C

実験手順

160.8 g of N-methylvanillylamine and 54 g of sodium cyanide are suspended in 1 liter of dimethylsulphoxide and dissolved by heating to 125°C. At this temperature, a solution of 100 ml of glacial acetic acid in 200 ml of water is added and the mixture is stirred for a further 2 hours under nitrogen at 125°C. It then cooled to 80°C and the dimethylsulphoxide is distilled off in a water-pump vacuum. 900 ml of water are added to the residue which is extracted with 350 ml of chloroform. The chloroform phase is extracted by shaking with water and dried with sodium sulphate. On distilling off the chloroform in vacuo, an oil is obtained, which is cooled and seeded. The crystals formed melt at 53°-54°C (boiling point0.1 :140°-144°C). The yield is 143 g (94% of theory).

後処理

  1. dissolutiondissolved
  2. temperatureIt then cooled to 80°C
  3. distillationthe dimethylsulphoxide is distilled off in a water-pump vacuum
  4. addition900 ml of water are added to the residue which
  5. extractionis extracted with 350 ml of chloroform
  6. extractionThe chloroform phase is extracted
  7. stirringby shaking with water
  8. dry with materialdried with sodium sulphate
  9. distillationOn distilling off the chloroform in vacuo
  10. customan oil is obtained
  11. temperaturewhich is cooled
  12. customThe crystals formed
  13. custommelt at 53°-54°C
  14. custom(boiling point0.1 :140°-144°C)

出典と根拠

ORDレコード
ord-cf0952bb1b0b45c9a0f3002a03677194
出典データセット
uspto-grants-1976_09
特許番号
US03983151

関連ノート

読み込み中…