Furan → 2-Dodecylfuran

HRID 1111421Notes

Reaction equation

HRID 1111421 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[Cl-].[NH4+]>CCCCCC.CCOCC>[CH2:23]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

7

Reactant 4

HCID 8029FuranHCID 89191-BromododecaneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 125641122-Dodecylfuran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A mixture of 68.1 g (1.0 mole) of furan and 500 ml of anhydrous ether is stirred at -20° C. after which 1.1 moles (458 ml of a 2.4 molar hexane solution) of butyllithium is added slowly with stirring. The reaction mixture is stirred for 1 hour, then 284 g (1.2 moles) of 1-bromododecane is added. The reaction mixture is stirred at room temperature for 4 hours after which it is poured into a saturated ammonium chloride solution. The organic layer is separated and washed with water and brine, dried over sodium sulfate and distilled under reduced pressure to give 2-dodecylfuran.

Workup

  1. additionis added slowly
  2. stirringThe reaction mixture is stirred for 1 hour
  3. stirringThe reaction mixture is stirred at room temperature for 4 hours after which it
  4. customThe organic layer is separated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-dac5b80235454401afd8de3dd5c3a0bd
Source dataset
uspto-grants-1990_12
Patent number
US04980371

Reaction notes

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