Benzyl Alcohol → 2-Furancarboxylic acid, tetrahydro-, phenylmethyl ester

HRID 1708565

Reaktionsgleichung

Reaktionsgleichung von HRID 1708565
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6](Cl)=[O:7].[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1>CCOCC>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 551254Tetrahydro-2-furancarbonyl chloride

Produkt 1

HCID 112872082-Furancarboxylic acid, tetrahydro-, phenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Tetrahydrofuroyl chloride (15.0 g, 112 mmol) was added dropwise to a cold solution of benzyl alcohol (10.9 g, 101 mmol) and pyridine (20.0 g, 253 mmol) in Et2O (200 mL). The solution was stirred at 0° for 40 minutes, then filtered to remove the side product pyridine hydrochloride. The filtrate was washed with 0.1M HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL), and then dried over MgSO4. Filtration and evaporation of the solvent gave a yellow oil, which was distilled. Benzyl tetrahydrofuroate was obtained as a colorless oil (21.1 g), b.p. 118° to 120° at 0.5 mm Hg. Microanalysis calc'd for C12H14O3 (206.2): C, 69.89; H, 6.84; O, 23.27; Found: C, 69.62; H, 6.89.

Aufarbeitung

  1. filtrationfiltered
  2. customto remove the side product pyridine hydrochloride
  3. washThe filtrate was washed with 0.1M HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and evaporation of the solvent
  6. customgave a yellow oil, which
  7. distillationwas distilled

Quellen und Nachweise

ORD-Eintrag
ord-b3e1060bd6f9438ab665a221ca63788e
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05359077

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