4-Formylbenzoic acid → HCID 54378189, compound

HRID 1283069Notes

Reaction equation

HRID 1283069 reaction equation
[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]

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 4137393Benzo[b]thiophene, 2-(4-methylphenyl)-HCID 23665647Potassium tert-butoxide2×

Product 1

HCID 54378189HCID 54378189, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
35 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cfbbcb501538499b95e6a0ae085a8e38
Source dataset
uspto-grants-1976_08
Patent number
US03974144

Reaction notes

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