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

HRID 2181391노트

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HRID 2181391 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 7855AcrylonitrileHCID 9237Dabco

생성물 1

HCID 112404803-Hydroxy-4-methyl-2-methylenepentanenitrile수율 193.4%

시약·촉매·용매 2

HCID 314042,6-Di-tert-butyl-4-methylphenol촉매HCID 962Water용매2회

반응 조건

온도
25 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-b854180c65674e99b1960f110e2d9bdc
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06891059B2

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