P-Toluic Acid → 4-(Bromomethyl)benzoic acid

HRID 1955464Notes

Reaction equation

HRID 1955464 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7470P-Toluic AcidHCID 67184N-bromobutanimide

Product 1

HCID 225994-(Bromomethyl)benzoic acidYield 65.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

39.7 g (287 mmmol) of p-toluylic acid, 51.2 g (287 mmmol) of N-bromosuccinimide and 2.8 g (11.5 mmol) of dibenzoyl peroxide were suspended in 350 ml of carbon tetrachloride. Then, the resultant mixture was heated with vigorously stirring to perform a reaction under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled in ice bath. The deposited crystalline product was collected by filtration, which was then washed with hexane and water, followed by drying. The resultant crystalline product was recrystallized from ethanol to obtain 40.3 g of 4-bromomethylbenzoic acid as a white needle crystal (isolated yield: 65%).

Workup

  1. customa reaction
  2. temperatureunder reflux for 2 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled in ice bath
  5. filtrationThe deposited crystalline product was collected by filtration, which
  6. washwas then washed with hexane and water
  7. customby drying
  8. customThe resultant crystalline product was recrystallized from ethanol
  9. customto obtain

Sources & evidence

ORD record
ord-99dfc4110d9f4ff8b51c87afc8a532eb
Source dataset
uspto-grants-1998_07
Patent number
US05776365

Reaction notes

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