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Sulfuric Acid → 4-Ethyl-3-iodo-alpha,alpha-dimethylbenzeneacetic acid

HRID 61873
ノート
印刷プレビュー

反応式

HRID 61873 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)[CH3:2].[I:15]N1C(=O)CCC1=O.S(=O)(=O)(O)O.S([O-])(O)=O.[Na+]>C(O)(=O)C.O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:14])[C:10]([OH:12])=[O:11])=[CH:5][C:4]=1[I:15])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 23665763Sodium BisulfiteHCID 581284462-(4-Ethylphenyl)-2-methylpropanoic acid

生成物 1

HCID 668346094-Ethyl-3-iodo-alpha,alpha-dimethylbenzeneacetic acid

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒
HCID 962
Water
溶媒

実験手順

2-(4-Ethylphenyl)-2-methylpropanoic acid (58.1 g, 302.2 mmol) was dissolved in acetic acid (175 ml), added with N-iodosuccinimide (71.4 g, 317.3 mmol, 1.05 eq.) and conc. sulfuric acid (75 ml) at 0° C. Thereafter, the mixture was stirred at room temperature for 2 hrs. After cooling the reaction solution to 0° C., 10% aqueous solution of sodium hydrogen sulfite (100 ml) was added and the mixture was stirred for 1 hr. H2O (450 ml) was added to the mixture and the precipitated solid was filtered to obtain the title compound as a crude product. Ethanol (150 ml) and 10% aqueous solution of sodium hydrogen sulfite (50 ml) were added to the crude product, and the mixture was dissolved under heating at 50° C. After confirming the dissolution, the solution was cooled to room temperature, added with H2O (300 ml), and then stirred at 0° C. for 1 hr. The precipitated solid was filtered to obtain the title compound (95.8 g, 99%).

後処理

  1. temperatureAfter cooling the reaction solution to 0° C.
  2. stirringthe mixture was stirred for 1 hr
  3. filtrationthe precipitated solid was filtered

出典と根拠

ORDレコード
ord-7ecfbe74d2a1453daec63b9ce67009ba
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440922B2

反応ノート

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