Orcinol → 7-Hydroxy-2,2,5-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one

HRID 2380914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2380914
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:10][C:11]([CH3:16])=[CH:12][C:13](O)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-].P(Cl)(Cl)(Cl)=O>>[OH:8][C:6]1[CH:5]=[C:4]2[C:3]([C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:10])[O:9]2)=[C:2]([CH3:1])[CH:7]=1

Komponenten

5

Edukt 4

HCID 10436OrcinolHCID 109313-Methyl-2-butenoic acidHCID 24813Phosphorus oxychlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 27279647-Hydroxy-2,2,5-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one

Versuchsvorschrift

Anhydrous 5-methylbenzen-1,3-diol (3.678 g), 3,3-dimethylacrylic acid (3.3 mL) and aluminum chloride (14.76 g) were added to phosphoryl chloride (45 mL) and the mixture was shaken at room temperature for 6 hours. The reaction solution was poured into ice, and the precipitates were filtered, washed with water and dried. The precipitates were purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=25/1) to give the titled compound (3.8 g) as a colorless powder.

Aufarbeitung

  1. additionThe reaction solution was poured into ice
  2. filtrationthe precipitates were filtered
  3. washwashed with water
  4. customdried
  5. customThe precipitates were purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=25/1)

Quellen und Nachweise

ORD-Eintrag
ord-f22bcebf65a347808aeaa44d6faa6d16
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258131B2

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