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Hydrochloric Acid → 8-(propan-2-yl)-3,4-dihydro-2H-1-benzopyran-4-one

HRID 1819505
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1819505
[CH:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[O:6][CH2:7][CH2:8][C:9]([OH:11])=O)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl.CN(C=O)C>[CH:1]([C:4]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:5]=1[O:6][CH2:7][CH2:8][C:9]2=[O:11])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 167772793-[2-(Propan-2-yl)phenoxy]propanoic acid

Produkt 1

HCID 231190888-(propan-2-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

3-(2-Isopropylphenoxy)propionic acid (11) was dissolved in dichloromethane (30 mL), and to the mixture were added oxalyl chloride (2.1 g) and DMF (5 mL) under ice-cooling. The reaction mixture was stirred for 30 minutes and cooled at −20° C. To the reaction mixture was added aluminium chloride (4 g), and the reaction mixture was stirred at −20° C. for 2 h. To the reaction mixture was added 2N hydrochloric acid, and the reaction mixture was extracted with dicloromethane. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1) to obtain the compound (12) 2.3 g.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at −20° C. for 2 h
  3. extractionthe reaction mixture was extracted with dicloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-e39558ed39c74c57b61429847866e967
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07601746B2

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