Butyl bromide → piperonyl butyl ether

HRID 2103741Notes

Reaction equation

HRID 2103741 reaction equation
[H-].[Na+].[CH2:3]([OH:13])[C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1.Br[CH2:15][CH2:16][CH2:17][CH3:18]>O1CCCC1>[CH2:15]([O:13][CH2:3][C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 10322Piperonyl alcoholHCID 24758Sodium hydride

Product 1

HCID 10013282piperonyl butyl etherYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

4 g of sodium hydride (60%) and 100 ml of tetrahydrofuran (THF) were stirred in a nitrogen stream. Thereto was dropwise added, in 30 minutes, 15.2 g (0.1 mol) of piperonyl alcohol dissolved in 70 ml of THF, followed by stirring for 30 minutes. Thereto was dropwise added 13.7 g (0.1 mol) of 1-bromobutane dissolved in THF, followed by stirring for 12 hours. The stirring was stopped and the reaction mixture was concentrated. The concentrate was dropped into an excess amount of a 2 N aqueous hydrochloric acid solution. Heptane was added thereto for extraction. The extract was washed with water until the washings became neutral, and then concentrated. The concentrate was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain 8.0 g of piperonyl butyl ether at a yield of 38.5% as a transparent oily substance.

Workup

  1. additionThereto was dropwise added, in 30 minutes
  2. stirringby stirring for 12 hours
  3. concentrationthe reaction mixture was concentrated
  4. additionThe concentrate was dropped into an excess amount of a 2 N aqueous hydrochloric acid solution
  5. additionHeptane was added
  6. extractionfor extraction
  7. washThe extract was washed with water until the washings
  8. concentrationconcentrated
  9. customThe concentrate was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-577e0c836b344dddb6a54d942031d1f8
Source dataset
uspto-grants-2009_08
Patent number
US07576125B2

Reaction notes

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