Реакция #2175455

Уравнение реакции

9-fluorenone-2,7-dicarboxylic acid

HCl

NaOH

hydrazine hydrate

→

2,7-fluorenedicarboxylic acid

Растворители

diethylene glycol

water

Условия реакции

Обработка

1. 1
   ДругоеIn an argon-purged flask
2. 2
   Другоеwas placed in a room temperature
3. 3
   ТемператураThe reaction mixture was slowly heated to 110 C
4. 4
   Температураrefluxed for approximately four hours
5. 5
   ТемператураThe reaction mixture was cooled
6. 6
   ФильтрацияThe product was filtered
7. 7
   Промывкаwashed with water
8. 8
   workup.DISSOLUTIONProduct was dissolved in warm NaOH solution (0.5M, warm)
9. 9
   Другоеprecipitated by acidification to pH 2 with HCl
10. 10
    ФильтрацияThe product was filtered
11. 11
    Промывкаwashed with water

Методика

In an argon-purged flask, 9-fluorenone-2,7-dicarboxylic acid (10.0 g, 0.037 mol) was suspended in diethylene glycol (75 mL). The flask was placed in a room temperature oil bath then NaOH (6.2 g, 0.155 mol) and an 80% solution of hydrazine hydrate (7.4 mL, 0.12 mol) were added successively. The reaction mixture was slowly heated to 110 C and refluxed for approximately four hours. The reaction mixture was cooled, carefully poured into water and acidified to pH 2 with concentrated HCl. The product was filtered and washed with water. Product was dissolved in warm NaOH solution (0.5M, warm) and precipitated by acidification to pH 2 with HCl. The product was filtered and washed with water. Product was an yellow solid (9.0 g, 96%). 1H-NMR (d6-DMSO): δ (ppm) 8.2 (s, 2H, Ar); 8.1 (m, 2H, Ar); 8.0 (m, 2H, Ar); 4.1 (s, 2H, CH2).

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