1-Bromopentane → HCID 15122333, compound

HRID 485226Notes

Reaction equation

HRID 485226 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7].[OH-].[Na+].Br[CH2:17]CCCC>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][O:7][CH:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 37463482-Furyl(phenyl)methanol

Product 1

HCID 15122333HCID 15122333, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

9 grams of the distilled 1-furyl-1-phenyl-methanol (0.052 mole) is charged to a reactor with 0.39 g (2 mole percent) tetrabutylammonium iodide and 10.4 g of a 50 percent aqueous solution of sodium hydroxide added over a 10 minute period with stirring. This is followed by addition of 17.6 g (0.14 mole) 1-bromopentane over a period of 10 minutes and the reaction mixture allowed to stir for 2 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-(methoxy, phenylmethyl)furan in low yield.

Workup

  1. additionadded over a 10 minute period
  2. stirringto stir for 2 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-5fe7c36c7dab4d1d8f9e720c48df498d
Source dataset
uspto-grants-1985_08
Patent number
US04536349

Reaction notes

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