Acetonitrile → 1-(2,4-Bis(benzyloxy)-5-isopropylphenyl)ethanone

HRID 334891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 334891
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[C:15](#N)C.C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCOC(C)=O.[CH3:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>>[CH2:24]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH2:15][C:40]2[CH:39]=[CH:38][CH:43]=[CH:42][CH:41]=2)[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

6

Edukt 5

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 247733601-(2,4-Dihydroxy-5-isopropylphenyl)ethanone

Produkt 1

HCID 247733611-(2,4-Bis(benzyloxy)-5-isopropylphenyl)ethanone

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a mixture of 1-(2,4-dihydroxy-5-isopropyl-phenyl)-ethanone (3.2 g), acetonitrile (60 ml) and potassium carbonate (10.6 g) in a a 250 ml single neck RB flask equipped with a reflux condenser and a guard tube was added benzyl bromide (9.1 ml). The reaction mixture was refluxed (90° C.) for 16 h. The progress of the reaction was monitored by TLC (10% EtOAc/n-hexane, product Rf-0.5). On completion, acetonitrile was removed under reduced pressure. Water (100 ml) was added to the residue obtained and the resulting mixture was extracted with ethyl acetate (200 ml). The organic layer was dried over sodium sulphate. The solvent was removed under reduced pressure to give a residue to which n-hexane (150 ml) was added to give the product.

Aufarbeitung

  1. customequipped with a reflux condenser and a guard tube
  2. customOn completion, acetonitrile was removed under reduced pressure
  3. additionWater (100 ml) was added to the residue
  4. customobtained
  5. extractionthe resulting mixture was extracted with ethyl acetate (200 ml)
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customThe solvent was removed under reduced pressure
  8. customto give a residue to which n-hexane (150 ml)
  9. additionwas added
  10. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-f28ae47f52b64f1fad41f41e7692e7d9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883790B2

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