1-Bromopentane → 2-(1-Pentoxyethyl)furan

HRID 485225

Reaction equation

HRID 485225 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:8])[CH3:7].[OH-].[Na+].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:12]([O:8][CH:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH3:7])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 1072431-(2-Furyl)ethanol

Product 1

HCID 202698962-(1-Pentoxyethyl)furan

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

Ten grams of the distilled 1-furylethanol (0.089 mole) is charged to a reactor with 0.61 g (2 mole percent) tetrabutylammonium bisulfate and 19.2 g of a 50 percent aqueous solution of sodium hydroxide added over a 15 minute period with stirring. This is followed by addition of 34.7 g (0.25 mole) 1-bromopentane over a period of 15 minutes and the reaction mixture allowed to stir for 3 hours. The reaction mixture is then extracted with diethyl ether which, after drying over magnesium sulfate, is evaporated. The resulting crude product is short-path distilled to obtain 2-(1-pentoxyethyl)furan in low yield (B.p. 35° C. at 0.2 mm Hg.). The structure of the 2-(1-pentoxyethyl)furan ##STR5## is confirmed by infrared and nuclear magnetic resonance spectroscopy.

Workup

  1. additionadded over a 15 minute period
  2. stirringto stir for 3 hours
  3. extractionThe reaction mixture is then extracted with diethyl ether which
  4. dry with materialafter drying over magnesium sulfate
  5. customis evaporated
  6. distillationThe resulting crude product is short-path distilled

Sources & evidence

ORD record
ord-19a8ea04c1314eceab388a6878981fce
Source dataset
uspto-grants-1985_08
Patent number
US04536349

Linked notes

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