Salicylic Acid → Benzyl Salicylate

HRID 1259016

Reaktionsgleichung

Reaktionsgleichung von HRID 1259016
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7]Br)=[CH:3][CH:2]=1.[C:9]([OH:18])(=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12].O>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:12][C:11]1[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=1[C:9]([O:18][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:17]

Komponenten

5

Edukt 3

HCID 338Salicylic AcidHCID 962WaterHCID 7498Benzyl Bromide

Produkt 1

HCID 8363Benzyl SalicylateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2724141Tetrabutylammonium FluorideLösungsmittel

Versuchsvorschrift

BnBr (1.75 mL, 14.631 mmol) was added to a solution of salicylic acid (2.0 g, 14.625 mmol) in TBAF (17.5 mL, 1 M solution in THF) and the reaction mixture was stirred at r.t. overnight (16 h). The organic layer was poured into H2O (100 mL) and extracted with EtOAc (70 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (2% EtOAc/hexanes) to furnish 2.53 g of benzyl 2-hydroxybenzoate (colourless oil, yield: 76%).

Aufarbeitung

  1. extractionextracted with EtOAc (70 mL)
  2. dry with materialIt was dried over Na2SO4 (anhydrous)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on SiO2 (2% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0f302b53436d46b8bb7f6b02c2d94567
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466197B2

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