Sodium Carbonate → 4-Hydroxymethyl-3-nitrobenzoic acid

HRID 1881655Notes

Reaction equation

HRID 1881655 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].C(=O)([O-])[O-:16].[Na+].[Na+]>O.CC(C)=O>[OH:16][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 1323864-Bromomethyl-3-nitrobenzoic acid

Product 1

HCID 15018924-Hydroxymethyl-3-nitrobenzoic acidYield 95.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4-Bromomethyl-3-nitrobenzoic acid (3.00 g, 11.5 mmol) and sodium carbonate (6.12 g, 57.7 mmol) were dissolved in water (40 mL) and acetone (40 mL). The reaction mixture was refluxed for 4 hours and then concentrated under reduced pressure to remove acetone. The residue was washed with diethyl ether three times. The aqueous layer was acidified with 6M hydrochloric acid, and then extracted with ethyl acetate three times. The combined organic layer was washed with water and brine, dried with sodium sulfate, filtered, concentrated under the reduced pressure. The residue was dried by means of a vacuum pump to give the desired product as brown solid (2.17 g, yield 95%).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customto remove acetone
  4. washThe residue was washed with diethyl ether three times
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic layer was washed with water and brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under the reduced pressure
  10. customThe residue was dried by means of a vacuum pump

Sources & evidence

ORD record
ord-ddac2847465e44ccadfeb7fb805ae793
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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