6-Methyl-2-nitrobenzoic acid → (2-Methyl-6-nitrophenyl)methanol

HRID 1579992Notes

Reaction equation

HRID 1579992 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4](O)=[O:5]>O1CCCC1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[CH2:4][OH:5]

Participants

3

Reactant 1

HCID 160976-Methyl-2-nitrobenzoic acid

Product 1

HCID 12204069(2-Methyl-6-nitrophenyl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° solution of 54.30 g (0.30 moles) of 2-methyl-6-nitrobenzoic acid in 500 ml of anhydrous tetrahydrofuran was added dropwise under a nitrogen atmosphere, 380 ml (0.38 moles) of a stock IM boran/THF solution at such a rate that the temperature did not exceed 5°. Upon complete addition, the ice bath was removed, the solution allowed to stir at room temperature for 14 hours, heated to reflux for 4 hrs. and then cooled to 0° in an ice bath. The reaction was quenched by the dropwise addition of 400 ml of 10% hydrochloric acid, the solution heated to reflux on a steam bath for 0.5 hrs., the THF solvent distilled at atmospheric pressure and the insoluble precipitate extracted into methylene chloride. The methylene chloride extracts were combined, washed with satd. sodium bicarbonate solution, dried (Na2SO4) and the solvent removed in vacuo affording a reddish colored semi solid. Purification was effected from 300 ml of carbon tetrachloride resulting in 41.35 g (84% yield) of yellow flakes; mp 67°-8°.

Workup

  1. customdid not exceed 5°
  2. additionUpon complete addition
  3. customthe ice bath was removed
  4. temperatureheated
  5. temperatureto reflux for 4 hrs
  6. temperatureand then cooled to 0° in an ice bath
  7. customThe reaction was quenched by the dropwise addition of 400 ml of 10% hydrochloric acid
  8. temperaturethe solution heated
  9. temperatureto reflux on a steam bath for 0.5 hrs
  10. distillation, the THF solvent distilled at atmospheric pressure
  11. extractionthe insoluble precipitate extracted into methylene chloride
  12. washwashed with satd
  13. dry with materialsodium bicarbonate solution, dried (Na2SO4)
  14. customthe solvent removed in vacuo
  15. customaffording a reddish colored semi solid
  16. customPurification

Sources & evidence

ORD record
ord-22f8833845da41d8900c4e6335b90971
Source dataset
uspto-grants-1976_01
Patent number
US03932407

Reaction notes

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