Benzyl Bromide → 2-(1,3-Dioxolan-2-yl)-1-benzylpyridinium bromide

HRID 742439Notes

Reaction equation

HRID 742439 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[CH2:12]([Br:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)(=O)C>[Br-:19].[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 797732-Pyridinyl-1,3-dioxolane

Product 1

HCID 190474902-(1,3-Dioxolan-2-yl)-1-benzylpyridinium bromideYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 716 g (4.74 mol) of 2-(1,3-dioxolan-2-yl)pyridine and 859 g (5 mol) of benzyl bromide in a 5 L flask was heated on a steam-bath to 80° C. where an exothermic reaction caused the reaction temperature to reach 146° C. The reaction mixture was allowed to cool to 90° C. and the mixture was heated on a steam-bath for 2 h. The reaction mixture was cooled to room temperature, the resulting solid product was heated on a steam-bath with ethyl acetate, and ethyl acetate was decanted. The treatment with ethyl acetate was repeated three times to afford 1526.8 g of 2-(1,3-dioxolan-2-yl)-1-benzylpyridinium bromide (Formula VI: R1 =R2 =R7 =H; Z- --=Br-).

Workup

  1. customan exothermic reaction
  2. customto reach 146° C
  3. temperatureto cool to 90° C.
  4. temperaturethe mixture was heated on a steam-bath for 2 h
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customwas decanted

Sources & evidence

ORD record
ord-0bda5bb9a3cc4775aba331ed2d27b645
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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