Water → Ethyl 2,4-dimethyl[1,1'-biphenyl]-3-carboxylate

HRID 1153843

반응식

HRID 1153843 반응식
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCOCC1.O.[CH3:17][C:18]1[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:22]([CH3:29])OC(=O)[CH:19]=1>C1(C)C=CC=CC=1>[CH3:29][C:22]1[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:18]([CH3:19])[CH:17]=[CH:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 998PhenylacetaldehydeHCID 8083MorpholineHCID 76918ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

생성물 1

HCID 13126289Ethyl 2,4-dimethyl[1,1'-biphenyl]-3-carboxylate수율 55.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A stirred solution of phenylacetaldehyde (77.0 g, 0.64 mole) and morpholine (56.0 g, 0.64 mole) in toluene (500 ml) was heated at reflux until the theoretical amount of water was collected in a Dean-Stark trap. The reaction mixture was cooled slightly, and ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (125.0 g, 0.64 mole) was added. The solvent was distilled from the reaction mixture at atmospheric pressure to leave a residue. The residue was then heated at 200° for 2.5 hours. A Dean-Stark trap was used to collect the distilled morpholine. The remaining pot residue was cooled and slurried with a mixture of silica gel (700 g) and methylene chloride (1500 ml) for 45 minutes. The slurry was filtered and the filter cake rinsed with methylene chloride (500 ml). The combined filtrates were evaporated under reduced pressure to leave a thick brown residue. This residue was distilled under reduced pressure to give several fractions. All fractions which contained more than 73% product by gc analysis were combined to give a total of 90.5 g crude ethyl 2,4-dimethyl-[1,1'-biphenyl]-3-carboxylate.

후처리

  1. customwas collected in a Dean-Stark trap
  2. temperatureThe reaction mixture was cooled slightly
  3. distillationThe solvent was distilled from the reaction mixture at atmospheric pressure
  4. customto leave a residue
  5. temperatureThe residue was then heated at 200° for 2.5 hours
  6. distillationto collect the distilled morpholine
  7. temperatureThe remaining pot residue was cooled
  8. additionslurried with a mixture of silica gel (700 g) and methylene chloride (1500 ml) for 45 minutes
  9. filtrationThe slurry was filtered
  10. washthe filter cake rinsed with methylene chloride (500 ml)
  11. customThe combined filtrates were evaporated under reduced pressure
  12. customto leave a thick brown residue
  13. distillationThis residue was distilled under reduced pressure
  14. customto give several fractions

출처 및 근거

ORD 기록
ord-34562dd3138241a699e716d8cd4ad8fd
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04486588

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