Hydrochloric Acid → 3-Hydroxy-4-methyl-2-methylenepentanenitrile

HRID 2181391ノート

反応式

HRID 2181391 の反応式
[N:1]12[CH2:8][CH2:7]N(CC1)CC2.[CH:9](=[O:13])[CH:10]([CH3:12])[CH3:11].[C:14](#N)C=C.Cl>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.O>[OH:13][CH:9]([CH:10]([CH3:12])[CH3:11])[C:7](=[CH2:14])[C:8]#[N:1]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 7855AcrylonitrileHCID 9237Dabco

生成物 1

HCID 112404803-Hydroxy-4-methyl-2-methylenepentanenitrile収率 193.4%

試薬・触媒・溶媒 2

HCID 314042,6-Di-tert-butyl-4-methylphenol触媒HCID 962Water溶媒2 回

反応条件

温度
25 °C

実験手順

A 250 mL, three-necked, round-bottom flask with overhead stirring is charged with 0.36 g (1.6 mmol) of 2,6-di-tert-butyl-4-methylphenol, 37 g (0.33 mol) of 1,4-diazabicyclo[2,2,2]octane, 60 mL (0.66 mol) of isobutyraldehyde, 52 mL (0.79 mol) of acrylonitrile, and 7.2 mL (0.4 mol) of water. The reaction mixture is stirred at 50° C. for 24 hours, cooled to 25° C., and quenched into a solution of 33 mL (0.38 mol) of hydrochloric acid and 100 mL of water. The product is extracted with 120 mL of methylene chloride. The aqueous acid layer is extracted again with 25 mL of methylene chloride. The combined methylene chloride layers are concentrated by rotary evaporation to provide 79.9 g (96.7%) of 3-hydroxy-4-methyl-2-methylenepentanenitrile as a yellow oil (which may solidify to a white solid on standing), 96.7% (area under the curve) by HPLC assay, which may be used in the next step without further purification. Carbonic acid 2-cyano-1-isopropyl-allyl ester ethyl ester

後処理

  1. stirringThe reaction mixture is stirred at 50° C. for 24 hours
  2. extractionThe product is extracted with 120 mL of methylene chloride
  3. extractionThe aqueous acid layer is extracted again with 25 mL of methylene chloride
  4. concentrationThe combined methylene chloride layers are concentrated by rotary evaporation

出典と根拠

ORDレコード
ord-b854180c65674e99b1960f110e2d9bdc
出典データセット
uspto-grants-2005_05
特許番号
US06891059B2

反応ノート

読み込み中…