1,3-Dibromopropane → [4-(Allyloxy)butyl]benzene

HRID 2424840Notes

Reaction equation

HRID 2424840 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:13][CH2:14][CH2:15]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH2:15]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 76889Benzenebutanol

Product 1

HCID 67246079[4-(Allyloxy)butyl]benzeneYield 250.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8058HexaneSolvent

Procedure

To a solution of 4-phenylbutan-1-ol (0.60 g, 3.99 mmol) in 1,3-dibromopropane (2.14 mL, 10.60 mmol) was added tetrabutylammonium bromide (20 mg, 0.064 mmol) and 50% sodium hydroxide (1.5 mL). The mixture was stirred at room temperature overnight. The crude reaction was diluted with n-hexane (20 mL) and washed with water (2×10 mL), dried (Na2SO4), and the solvent removed under reduced pressure. The title compound (1.90 g, 92% purity) was obtained by distillation of the residue under reduced pressure and was used in the next step without further purification.

Workup

  1. customThe crude reaction
  2. washwashed with water (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bced35568b9d4c5db89d0627fb1a5948
Source dataset
uspto-grants-2011_06
Patent number
US07964615B2

Reaction notes

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