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

HRID 61873
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 61873
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7ecfbe74d2a1453daec63b9ce67009ba
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440922B2

Notizen zur Reaktion

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