Salicyl Alcohol → Benzenemethanol, 2-(phenylmethoxy)-

HRID 743378

Reaktionsgleichung

Reaktionsgleichung von HRID 743378
CC(C)([O-])C.[K+].[CH2:7]([OH:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[CH2:16]([O:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH2:7][OH:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 5146Salicyl AlcoholHCID 7498Benzyl BromideHCID 8058HexaneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 18811Benzenemethanol, 2-(phenylmethoxy)-Ausbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

151 g of potassium t-butoxide were added, whilst ice-cooling and stirring, to a solution of 152 g of salicyl alcohol in 600 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes; 160 ml of benzyl bromide were then added dropwise to the mixture. The reaction mixture was then stirred at a temperature of from 30° to 40° C. for 2 hours, after which it was partitioned between ethyl acetate and water. The organic layer was washed twice, each time with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was subjected to column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 228.5 g (yield 87%) of 2-benzyloxybenzyl alcohol as a colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. stirringThe reaction mixture was then stirred at a temperature of from 30° to 40° C. for 2 hours
  3. customafter which it was partitioned between ethyl acetate and water
  4. washThe organic layer was washed twice
  5. dry with materialeach time with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe oily residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-ca8ed899893e4c4988b0ee3b61efe071
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556864

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