Water → 3-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile

HRID 992668

반응식

HRID 992668 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][C:11]#[N:12].[CH:13](OCC)=[O:14].[O-]CC.[Na+].O>C(O)C>[OH:14][CH:13]=[C:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[C:11]#[N:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 8025Ethyl formateHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 2723922Sodium ethoxide

생성물 1

HCID 701428183-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile수율 98%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

A solution of 2,4,6-trimethylphenylacetonitrile (75 g) and ethyl formate (67 g) in 225 ml absolute ethanol was treated with solid sodium ethoxide (36 g) in small portions over 10 minutes, with good stirring. The mixture was heated to 60° C. under nitrogen for 16 hours and allowed to cool to room temperature. The reaction mixture was poured into 1.2 liters of water, extracted with diethyl ether (3×200 ml). The aqueous phase was acidified with 6 M HCl to pH=1 and extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over MgSO4 and concentrated, yielding 46 g (98%) of 3-hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile (intermediate 1).

후처리

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (3×200 ml)
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a2936e20d7a5450b9be65c7a0abc9c71
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469166B2

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