Phloroglucinol → 5,7-Dihydroxy-2,2-dimethylchroman-4-one

HRID 494956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494956
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([OH:23])[CH:17]=1.[CH3:24][C:25]([CH3:30])=[CH:26][C:27](O)=[O:28]>CS(O)(=O)=O>[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]2[C:17]=1[C:27](=[O:28])[CH2:26][C:25]([CH3:30])([CH3:24])[O:23]2

Komponenten

5

Edukt 3

HCID 359PhloroglucinolHCID 109313-Methyl-2-butenoic acidHCID 14812Phosphorus oxide (P4O10)

Produkt 1

HCID 8213625,7-Dihydroxy-2,2-dimethylchroman-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6395Methanesulfonic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

40 ml of methanesulfonic acid was added to 1.99 g of diphosphorus pentoxide under nitrogen atmosphere. Thereafter, a mixture consisting of 3.15 g of 1,3,5-trihydroxybenzene and 3,3-dimethylacrylic acid was added to the reaction solution at 70° C. The reaction solution was stirred at 70° C. for 30 minutes and then cooled to a room temperature. The reaction solution was added to ice water, followed by extraction with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 2.81 g of the subject compound.

Aufarbeitung

  1. additionwas added to the reaction solution at 70° C
  2. temperaturecooled to a room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e99c47404f834f2395e7687446602c1d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538123B2

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