Ethyl 3-phenylprop-2-enoate → 3-Cyano-3-phenylpropanoic acid

HRID 428339

反応式

HRID 428339 の反応式
[C:1]([O:11]CC)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C-:14]#[N:15].[K+].[Cl-].[NH4+]>CN(C=O)C>[C:14]([CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][C:1]([OH:11])=[O:10])#[N:15]

参加物

5

反応物 3

HCID 7649Ethyl 3-phenylprop-2-enoateHCID 9032Potassium CyanideHCID 25517Ammonium Chloride

生成物 1

HCID 111946253-Cyano-3-phenylpropanoic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
105 °C

実験手順

Ethyl cinnamate (85.3 g, 0.484 mol), potassium cyanide (64.2 g, 0.986 mol) and ammonium chloride (38.9 g, 0.726 mol) were mixed with aqueous DMF (90%, 360 mL). The mixture was stirred at 105° C. for 7 hours. The somewhat cooled mixture was filtered and most of the DMF was evaporated. The residue was taken up in diethyl ether and 1 M HCl. The aqueous phase was extracted twice with diethyl ether. The combined diethyl ether phases were evaporated and the black oil was suspended in EtOH (200 mL) and 2 M NaOH (250 mL) and stirred at ambient temperature for 2 hours. The mixture was diluted with brine (200 mL) and water (400 mL) and washed twice with diethyl ether. After acidification (12 M HCl) the aqueous phase was extracted three times with diethyl ether. The pooled organic phases were dried (Na2SO4) and the solvent evaporated affording the title compound as a black oil, 74 g (87%): 1H NMR (CDCl3) δ1.05 (d, 3H), 1.17 (d, 3H), 1.22 (d, 6H), 2.68 (dd, 1H), 3.16 (dd, 1H), 3.4 (br, 1H), 3.76 (m, 1H) 4.19 (dd, 1H), 7.31 (m, 5H), 8.9 (br, 1H).

後処理

  1. filtrationThe somewhat cooled mixture was filtered and most of the DMF
  2. customwas evaporated
  3. extractionThe aqueous phase was extracted twice with diethyl ether
  4. customThe combined diethyl ether phases were evaporated
  5. stirring2 M NaOH (250 mL) and stirred at ambient temperature for 2 hours
  6. additionThe mixture was diluted with brine (200 mL) and water (400 mL)
  7. washwashed twice with diethyl ether
  8. extractionAfter acidification (12 M HCl) the aqueous phase was extracted three times with diethyl ether
  9. dry with materialThe pooled organic phases were dried (Na2SO4)
  10. customthe solvent evaporated

出典と根拠

ORDレコード
ord-c4c8675097d5431abc0cfdd33feb52bf
出典データセット
uspto-grants-2001_11
特許番号
US06313132B1

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