Fluorobenzene → 2-(4-Fluorobenzoyl)-naphthalene-3-carboxylic acid

HRID 745894ノート

反応式

HRID 745894 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]2[C:11]([O:13][C:14](=[O:15])[C:2]=12)=[O:12].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:11]([C:3]2[C:2]([C:14]([OH:13])=[O:15])=[CH:1][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)=[O:12])=[CH:19][CH:18]=1

参加物

4

反応物 3

HCID 10008FluorobenzeneHCID 69743Naphtho(2,3-c)furan-1,3-dioneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 233109402-(4-Fluorobenzoyl)-naphthalene-3-carboxylic acid収率 113.8%

実験手順

45.0 g (227 mmol) of 2,3-naphthalenedicarboxylic acid anhydride are suspended in 200 ml (2.1 moles) of fluorobenzene. 75.5 g (565 mmol) of powdered aluminium chloride are added in the course of 5 minutes, with vigorous stirring (exothermic reaction up to about 32° C.). The dark red suspension is refluxed and stirred for 6 hours. The solution is then allowed to cool to room temperature and is poured onto about 500 g of ice, and is stirred to bring the hydrolysis to completion. Excess fluorobenzene is evaporated off and the resulting product is suspended in water. The suspension is filtered, the filtrate is rinsed with water and the product is dried. 76 g of crude 2-(4-fluorobenzoyl)-naphthalene-3-carboxylic acid are obtained. The crude product is stirred with 2 liters of 10% sodium carbonate solution, the resulting solution is acidified with hydrochloric acid and the white precipitate is filtered off and dried. 54.2 g (81% of theory) of 2-(4-fluorobenzoyl)-naphthalene-3-carboxylic acid are obtained.

後処理

  1. custom(exothermic reaction up to about 32° C.)
  2. temperatureThe dark red suspension is refluxed
  3. stirringstirred for 6 hours
  4. stirringis stirred
  5. customthe hydrolysis to completion
  6. customExcess fluorobenzene is evaporated off
  7. filtrationThe suspension is filtered
  8. washthe filtrate is rinsed with water
  9. customthe product is dried

出典と根拠

ORDレコード
ord-0ff564ee45564632a2bab757242902bb
出典データセット
uspto-grants-1986_07
特許番号
US04601853

反応ノート

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