Hydrochloric Acid → 1,4-Naphthalenedicarboxylic acid

HRID 354646ノート

反応式

HRID 354646 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[Cu]C#N.[OH-:18].[Na+].Cl.CN(C)[CH:23]=[O:24]>>[C:2]1([C:23]([OH:24])=[O:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 2825914-Bromo-1-naphthoic acidHCID 178418546HCID 178418546、化合物

生成物 1

HCID 690651,4-Naphthalenedicarboxylic acid

実験手順

125.6 parts by weight of 4-bromo-1-naphthoic acid with a melting point of 219°-220° and 51 parts by weight of copper-(I) cyanide (67-71% copper) are introduced into 330 parts by weight of dimethylformamide. The mixture is then heated under reflux for 4 hours, whilst stirring, to 150°-160° C., whereby, after some time, the solid materials go into solution, but then the 4-cyano-1-naphthoic acid copper bromide complex is gradually precipitated. After cooling to about 100°, the reaction mixture is diluted with 330 parts by weight of water and stirred for approximately one hour at room temperature, and the precipitate is filtered off by suction and rinsed with about 400 parts by weight of water. The 4-cyanonaphthoic acid/copper bromide complex thus isolated is introduced into 550 parts by weight of 20% sodium hydroxide solution and heated under reflux for 5 hours. The mixture is then adjusted to pH 7.0-7.5 with about 220 parts by weight of concentrated hydrochloric acid, the solution is filtered off by suction from the copper oxide slurry deposited and this slurry is rinsed with about 500 parts by weight of water, in portions. The naphthalene-1,4-dicarboxylic acid is precipitated from the filtrate at pH 2 by the addition of about 100 parts by weight of concentrated hydrochloric acid, and the precipitate is filtered off under suction and is washed with water until free of chloride ions. After drying, 92 parts by weight of a practically colorless naphthalene-1,4-dicarboxylic acid with a melting point of 315°-320° are obtained.

後処理

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 4 hours
  3. customthe 4-cyano-1-naphthoic acid copper bromide complex is gradually precipitated
  4. temperatureAfter cooling to about 100°
  5. additionthe reaction mixture is diluted with 330 parts by weight of water
  6. stirringstirred for approximately one hour at room temperature
  7. filtrationthe precipitate is filtered off by suction
  8. washrinsed with about 400 parts by weight of water
  9. customThe 4-cyanonaphthoic acid/copper bromide complex thus isolated
  10. temperatureheated
  11. temperatureunder reflux for 5 hours
  12. filtrationthe solution is filtered off by suction from the copper oxide slurry
  13. washthis slurry is rinsed with about 500 parts by weight of water, in portions
  14. customThe naphthalene-1,4-dicarboxylic acid is precipitated from the filtrate at pH 2 by the addition of about 100 parts by weight of concentrated hydrochloric acid
  15. filtrationthe precipitate is filtered off under suction
  16. washis washed with water until free of chloride ions
  17. customAfter drying

出典と根拠

ORDレコード
ord-bb6ecf0ad8274f85a6173067229ad541
出典データセット
uspto-grants-1983_03
特許番号
US04376214

反応ノート

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