Hydrochloric Acid → 2,4-Dimethyl-3-cyclohexene carboxaldehyde

HRID 1155253

反応式

HRID 1155253 の反応式
Cl[CH:2]([CH3:4])[CH3:3].[Mg:5].[CH3:6][CH:7]1[CH:12]=[C:11]([CH3:13])[CH2:10][CH2:9][CH:8]1[CH:14]=[O:15].[ClH:16]>CCOCC>[CH:2]([Mg:5][Cl:16])([CH3:4])[CH3:3].[CH3:6][CH:7]1[CH:12]=[C:11]([CH3:13])[CH2:10][CH2:9][CH:8]1[CH:14]=[O:15]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 63612-ChloropropaneHCID 933752,4-Dimethyl-3-cyclohexene carboxaldehydeHCID 5462224Magnesium

生成物 2

HCID 933752,4-Dimethyl-3-cyclohexene carboxaldehydeHCID 178418918HCID 178418918、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒4 回

反応条件

温度
0 °C

実験手順

A solution of isopropyl magnesium chloride in ether is prepared by dropwise adding a solution of 164 grams (2.1 moles) of 2-chloropropane in 200 ml of ether to a stirred slurry of 50 grams (2.1 moles) of magnesium in 500 ml of ether at reflux under nitrogen. The resulting solution is stirred at reflux for 30 minutes. A solution of 164 grams (2 moles) of 2,4-dimethyl-3-cyclohexenecarboxaldehyde in 200 ml of ether is added over a 45-minute period to the reaction mixture at reflux under nitrogen. The resulting slurry is heated at reflux for 30 minutes and then cooled to 0° C. 400 ml of 18% aqueous hydrochloric acid is slowly added with cooling and stirring. Two clear layers are formed. The aqueous layer is discarded and the organic layer is washed twice with H2O, neutralizing the second wash with aqueous caustic soda. The ether is removed by distillation at atmospheric pressure. Fractional distillation of the remaining oil (375 grams) through a 11/2"×12" Goodloe packed column affords 121 grams of recovered 2,4-dimethyl-3-cyclohexenecarboxaldehyde; 54 grams of 1,5-dimethyl-3-isopropyl-2-oxabicyclo[2.2.2]octane; and 173 grams of 2,4-dimethylalpha-isopropyl-3-cyclohexene-1-methanol (b.p. 91° C., 2.1 mm Hg pressure).

後処理

  1. temperatureat reflux under nitrogen
  2. temperatureat reflux for 30 minutes
  3. temperatureat reflux under nitrogen
  4. temperatureThe resulting slurry is heated
  5. temperatureat reflux for 30 minutes
  6. temperaturewith cooling
  7. stirringstirring
  8. customTwo clear layers are formed
  9. washthe organic layer is washed twice with H2O
  10. washsecond wash with aqueous caustic soda
  11. customThe ether is removed by distillation at atmospheric pressure
  12. distillationFractional distillation of the remaining oil (375 grams) through a 11/2"×12" Goodloe

出典と根拠

ORDレコード
ord-6887802de2fb4fa6a815ce01a55a4edd
出典データセット
uspto-grants-1981_11
特許番号
US04301024

関連ノート

読み込み中…