Water → HCID 53700676, compound

HRID 2227883Notes

Reaction equation

HRID 2227883 reaction equation
[OH-:1].[Na+].O.[CH:4]([CH:6](O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:5].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][O:1][CH2:5][CH:4]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 92986alpha-Vinylbenzyl alcohol

Product 1

HCID 53700676HCID 53700676, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

An amount of 20 g (0.5 mol) of sodium hydroxide and 20 ml of water were placed into a four-necked flask of 300 ml in capacity and then stirred to prepare a homogeneous solution. The temperature of this solution was reverted to room temperature, and then thereto a solution as prepared by dissolving 13.42 g (0.1 mol) of vinylbenzyl alcohol (mixture of m-isomer and p-isomer), 32.39 g (0.15 mol) of 1,4-dibromobutane, and 3.22 g (0.01 mol) of tetrabutylammonium bromide into 100 ml of toluene was added. While being vigorously stirred, the resultant mixed solution was allowed to react at 40° C. for 6 hours. Thereafter, the solution was separated and then sufficiently washed with water. The resultant organic layer was dried by adding thereto magnesium sulfate, and then toluene was distilled off under reduced pressure. The resultant solution was distilled in the presence of DPPH (diphenylpicryl-2-hydrazyl) under vacuum (boiling point: 125˜128° C./16 Pa) to obtain a colorless transparent liquid of 4-bromobutoxymethylstyrene. The yield amount was 15.0 g, and the yield ratio was 56 mol %.

Workup

  1. customto prepare a homogeneous solution
  2. customwas reverted to room temperature
  3. customa solution as prepared
  4. additionwas added
  5. stirringWhile being vigorously stirred
  6. additionthe resultant mixed solution
  7. customto react at 40° C. for 6 hours
  8. customThereafter, the solution was separated
  9. washsufficiently washed with water
  10. customThe resultant organic layer was dried
  11. additionby adding
  12. distillationmagnesium sulfate, and then toluene was distilled off under reduced pressure
  13. distillationThe resultant solution was distilled in the presence of DPPH (diphenylpicryl-2-hydrazyl) under vacuum (boiling point: 125˜128° C./16 Pa)

Sources & evidence

ORD record
ord-b3315b21c2744d95b981fbf7df1e558c
Source dataset
uspto-grants-2002_07
Patent number
US06414182B1

Reaction notes

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