Methyl Acrylate → Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate

HRID 1576197노트

반응식

HRID 1576197 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16]>C(O)(C)(C)C>[CH3:19][O:18][C:14](=[O:17])[CH2:15][CH2:16][C:11]([C:12]#[N:13])([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:16][CH2:15][C:14]([O:18][CH3:19])=[O:17]

참가 물질

4

반응물 2

HCID 7294Methyl AcrylateHCID 667273,4-Dimethoxybenzeneacetonitrile

생성물 1

HCID 1803855Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate수율 65.4%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

A mixture of 25 g. (0.141 mole) of the known compound (3,4-dimethoxyphenyl)acetonitrile and 66 ml. of methyl acrylate in 70 ml. of t-butyl alcohol is heated to reflux. The heat is removed and 21.5 ml. of 40% methanolic Triton B in 32 ml. of t-butyl alcohol quickly added. After about 4 hours of heating at reflux the mixture is allowed to cool and taken up in water and benzene. The organic layer is washed successively with 2.5 N hydrochloric acid, water and brine and then evaporated to dryness. The residue is distilled under vacuum, first at 40 mm. of mercury to remove excess methyl acrylate and then at 0.20 mm. to give 32.22 g. (65.4% yield) of dimethyl-4-cyano-4-(3,4-dimethoxyphenyl)pimelate, having a boiling point of 210° to 214°C. The NMR spectrum of the compound confirms its expected structure.

후처리

  1. additionA mixture of 25 g
  2. customThe heat is removed
  3. additionof t-butyl alcohol quickly added
  4. temperatureAfter about 4 hours of heating
  5. temperatureat reflux the mixture
  6. temperatureto cool
  7. washThe organic layer is washed successively with 2.5 N hydrochloric acid, water and brine
  8. customevaporated to dryness
  9. distillationThe residue is distilled under vacuum, first at 40 mm
  10. customof mercury to remove excess methyl acrylate
  11. customto give 32.22 g

출처 및 근거

ORD 기록
ord-0cec7b7a511f4a2d9fa27973322a5fc1
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03979444

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