Citric Acid → 3-Hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoic acid

HRID 1576411ノート

反応式

HRID 1576411 の反応式
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[OH:9][CH:10]1[CH2:14][C:13](=O)[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:11]1[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[OH:9][CH:10]1[CH2:14][C:13](=[N:2][OH:3])[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:11]1[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

7

反応物 5

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 681356993-Hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid

生成物 1

HCID 737949793-Hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a solution of 6.95 parts of hydroxylamine hydrochloride and 16.4 parts of sodium acetate dissolved in 80 parts by volume of 50% aqueous methanol is added a solution of 6.5 parts of 3-hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid and 0.8 parts of sodium hydroxide in 30 parts by volume of 50% aqueous methanol. That mixture is allowed to stand for 48 hours. After that time, the reaction mixture is acidified with citric acid and filtered to yield crystals which, when recrystallized from 50 parts by volume of methanol, gives 3-hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoic acid. That compound melts at about 164° and displays, in methanol, an ultraviolet absorption spectrum with a peak at about 321 millimicrons with a molecular extinction coefficient of about 44,700. That compound is represented by the following structural formula ##SPC10##

後処理

  1. filtrationfiltered
  2. customto yield crystals which, when
  3. customrecrystallized from 50 parts by volume of methanol

出典と根拠

ORDレコード
ord-8435445b68f2414dbac4879cd08eeb47
出典データセット
uspto-grants-1976_09
特許番号
US03980700

反応ノート

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