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

HRID 744906Notes

Reaction equation

HRID 744906 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 112872082-Furancarboxylic acid, tetrahydro-, phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c7c9294a49fb4a4faf2749416c6ce087
Source dataset
uspto-grants-1996_09
Patent number
US05559237

Reaction notes

Loading…