Benzoyl Peroxide → 2-Bromoethyl Benzoate

HRID 1614296Notes

Reaction equation

HRID 1614296 reaction equation
[C:1]1([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:7]([O:11][CH2:10][CH2:9][Br:12])(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 702932-Phenyl-1,3-dioxolane

Product 1

HCID 5230902-Bromoethyl Benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 120.14 grams (0.80 mol) of 2-phenyl-1,3-dioxolane, 142.39 grams (0.80 mol) of N-bromosuccinimide, 1 liter of carbon tetrachloride and a catalytic amount of benzoyl peroxide was heated with stirring at reflux for 5.25 hours and then cooled. The mixture was filtered, and the filtrate was concentrated to an oil. Distillation of this oil gave 147.8 grams; (80.65% of theory) of the product; bp=104°-111° C./0.40 mm.

Workup

  1. temperatureat reflux for 5.25 hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated to an oil
  5. distillationDistillation of this oil
  6. customgave 147.8 grams

Sources & evidence

ORD record
ord-8b03f7eeba064a9a912a661838e39a85
Source dataset
uspto-grants-1993_03
Patent number
US05196539

Reaction notes

Loading…