Water → 4-Methoxy-5-methyl-indan-1-one

HRID 1099371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1099371
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C)C=O>[CH3:13][O:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 668122914-Hydroxy-5-methyl-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 552973254-Methoxy-5-methyl-indan-1-oneAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

To a suspension of 4-Hydroxy-5-methyl-indan-1-one (50.0 gm, 0.308 mole) and Potassium carbonate (127.0 gm, 0.928 mole) in Dimethylformamide (250 ml), Dimethyl sulphate (90 ml, 0.928 mole) was added at 0° C. The reaction mixture was heated at 60-65° C. and stirred for 16 hours. The reaction mixture was poured into water (1 liter) and extracted with Ethylacetate (3×250 ml). The organic layer was dried over Sodium sulphate and distilled under vacuum to give 10.0 gm of crude product which was purified by column chromatography using Hexane as a mobile phase. The collected fractions were distilled under vacuum to give 45.0 gm of desired product as a viscous oil.

Aufarbeitung

  1. additionwas added at 0° C
  2. extractionextracted with Ethylacetate (3×250 ml)
  3. dry with materialThe organic layer was dried over Sodium sulphate
  4. distillationdistilled under vacuum
  5. customto give 10.0 gm of crude product which
  6. customwas purified by column chromatography
  7. distillationThe collected fractions were distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5185eb1bf97744f6ad70218e360e0109
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143424B2

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