Acetic Acid → 3-Bromo-4-propylbenzoic acid

HRID 46415

Reaction equation

HRID 46415 reaction equation
C(O)(=O)C.[N+]([O-])(O)=O.[CH2:9]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH2:10][CH3:11].[Br:21]Br>O.[N+]([O-])([O-])=O.[Ag+]>[CH2:9]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[Br:21])[CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 24408BromineHCID 1376014-Propylbenzoic acid

Product 1

HCID 203870433-Bromo-4-propylbenzoic acid

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 150 ml of glacial acetic acid, 33 ml of concentrated nitric acid and 25 ml of water, were added 8.2 g (0.05 moles) of parapropyl benzoic acid and 8.8 g (0.055 moles) of bromine. Then, at a temperature of 25° C., and over a period of half an hour, a solution of 8.5 g (0.05 moles) of silver nitrate in 25 cc of water was added. The solution was stirred for three hours, thirty minutes following which the suspended solid was removed by filtration and rinsed until neutral. Thereafter, the acid was dissolved in ethanol. Recrystallization from hexane yielded 4-propyl-3-bromo-benzoic acid.

Workup

  1. waitThen, at a temperature of 25° C., and over a period of half an hour
  2. customwas removed by filtration
  3. washrinsed until neutral
  4. dissolutionThereafter, the acid was dissolved in ethanol
  5. customRecrystallization from hexane

Sources & evidence

ORD record
ord-3a1733dc96d447078fc35cabe36a2cb0
Source dataset
uspto-grants-1979_11
Patent number
US04173545

Linked notes

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