4-Formylbenzoic acid → HCID 54378189, 화합물

HRID 1283069노트

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HRID 1283069 반응식
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[CH:3][CH:2]=1.[C:17]([OH:27])(=[O:26])[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>C(O)(=O)C>[C:17]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[CH:16][C:1]2[CH:2]=[CH:3][C:4]([C:7]3[S:8][C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[CH:11]=3)=[CH:5][CH:6]=2)=[CH:20][CH:19]=1)([OH:27])=[O:26]

참가 물질

5

반응물 3

HCID 120884-Formylbenzoic acidHCID 4137393Benzo[b]thiophene, 2-(4-methylphenyl)-HCID 23665647Potassium tert-butoxide2회

생성물 1

HCID 54378189HCID 54378189, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
35 °C

실험 절차

A stirred solution of 2.24 g (0.01 mole) of 2-(p-tolyl)benzothiophene and 2.25 g (0.01 mole) of the anil derivative of terephthalaldehydic acid in 150 ml of freshly distilled, dry dimethylformamide was flushed with nitrogen for 10 minutes. The solution was heated to 35°C and 6.72 g (0.06 mole) of potassium tert-but-oxide was added. The color of the reaction mixture changed from violet to brown. Analysis of an aliquot by ultraviolet spectroscopy showed that the reaction was completed after 2 hours of stirring. Glacial acetic acid was added in amount sufficient to neutralize excess potassium tert-butoxide, and the reaction mixture was heated to reflux and filtered while hot to collect the resulting precipitate. The filter cake was washed with hot dimethylformamide containing two percent aniline, then slurried in hot ten percent aqueous hydrochloric acid and refiltered. The collected precipitate was washed on the filter with water until free of acid and then dried in vacuo. The product was finally purified by sublimation to obtain 2-[4-(4-carboxystyryl)phenyl]benzothiophene which remained unmelted at 350°C. The wavelength of maximum excitation of this compound was 367 nm and the wavelength of maximum emission was 423 nm.

후처리

  1. customdry dimethylformamide was flushed with nitrogen for 10 minutes
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux
  4. filtrationfiltered while hot
  5. customto collect the resulting precipitate
  6. washThe filter cake was washed with hot dimethylformamide containing two percent aniline
  7. washThe collected precipitate was washed on the
  8. filtrationfilter with water until free of acid
  9. customdried in vacuo
  10. customThe product was finally purified by sublimation

출처 및 근거

ORD 기록
ord-cfbbcb501538499b95e6a0ae085a8e38
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03974144

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