Hydrochloric Acid → 3-Bromo-5-methylbenzoic acid

HRID 662043Notes

Reaction equation

HRID 662043 reaction equation
[O-][Mn](=O)(=O)=O.[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH2:15][OH:16])[CH:11]=[C:12]([CH3:14])[CH:13]=1.Cl.C(=O)(O)[O-:19].[Na+]>O.CC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]([CH:11]=[C:12]([CH3:14])[CH:13]=1)[C:15]([OH:19])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 22983157(3-Bromo-5-methylphenyl)methanol

Product 1

HCID 34331273-Bromo-5-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of KMnO4 (39.3 g, 249 mmol) in water (600 mL) was added slowly to a solution of (3-bromo-5-methylphenyl)methanol (25.0 g, 124 mmol) in acetone (500 mL). The mixture was kept at reflux for 60 mins. After cooling to room temperature, the mixture was acidified with HCl (2N, 100 mL). A brown precipitate formed and was dissolved by adding a solution of saturated sodium bicarbonate (100 mL); then acetone was evaporated in vacuum. Ammonia (150 mL) was added. The mixture was filtered over Celite and the filtrate acidified with concentrated HCl. The product was extracted with diethyl ether (3×150 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuum to obtain 16.0 g of the acid, 3-bromo-5-methylbenzoic acid, as white crystals (yield: 60%). 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.85-7.84 (m, 1H), 7.58 (s, 1H), 2.40 (s, 3H).

Workup

  1. temperatureat reflux for 60 mins
  2. customA brown precipitate formed
  3. dissolutionwas dissolved
  4. customthen acetone was evaporated in vacuum
  5. additionAmmonia (150 mL) was added
  6. filtrationThe mixture was filtered over Celite
  7. extractionThe product was extracted with diethyl ether (3×150 mL)
  8. dry with materialThe combined organic phases were dried (Na2SO4)
  9. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-49418c8dbd8a498ba94eec6a4afd83b1
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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