Acetic Acid → 4-Octyl-3-bromo-benzoic acid

HRID 904058Notes

Reaction equation

HRID 904058 reaction equation
[CH2:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:18]Br.[N+]([O-])(O)=O.C(O)(=O)C>O.C(O)C.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][C:17]=1[Br:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 19147p-Octylbenzoic acidHCID 24408Bromine

Product 1

HCID 233334464-Octyl-3-bromo-benzoic acidYield 54.3%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

7 g (0.03 mole) of p-octyl benzoic acid and 6.4 g (0.04 mole) of bromine are added to a mixture of 15 ml of deionized water, 20 ml of nitric acid and 90 ml of acetic acid, the temperature of which is 25° C. A solution of 5.1 g (0.03 mole) of silver nitrate in 15 ml of deionized water is then added over a period of half an hour. The solution is stirred for 3 hours 30 minutes, then the solid in suspension is filtered and washed with deionized water until the washing water shows a neutral reaction. The acid is dissolved in ethanol and the solution is bleached while hot with vegetable black. The crude product obtained after distillation of the ethanol is recrystallized in a 75% ethanol/25% water mixture. 5.1 g of pure product are obtained.

Workup

  1. customis 25° C
  2. filtrationthe solid in suspension is filtered
  3. washwashed with deionized water until the washing water
  4. customa neutral reaction
  5. customThe crude product obtained
  6. distillationafter distillation of the ethanol
  7. customis recrystallized in a 75% ethanol/25% water mixture

Sources & evidence

ORD record
ord-5397ef8141b34b0ca42cbdb5744f9324
Source dataset
uspto-grants-1980_10
Patent number
US04230596

Reaction notes

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