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

HRID 1589932Notes

Reaction equation

HRID 1589932 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].B.C1COCC1>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

4

Reactant 2

HCID 160976-Methyl-2-nitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 12204069(2-Methyl-6-nitrophenyl)methanolYield 107.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 100 mL round bottomed flask under dry argon was charged with 5 g of 2-methyl-6-nitrobenzoic acid which was dissolved in 60 mL of dry tetrahydrofuran. To this solution was added slowly with cooling and stirring, 64.17 mL of a 1M solution of BH3.THF in THF. The mixture was refluxed for 17 h then the reaction was slowly and carefully quenched with an excess of 10% aqueous hydrochloric acid. The THF was removed under vacuum and the residue was extracted with three 50 mL aliquots of methylene chloride. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and the solvent removed. The crude product was recrystallized from methylene chloride/pentane to give 4.95 g of yellowish crystals (97% yield).

Workup

  1. additionTo this solution was added slowly
  2. temperaturewith cooling
  3. temperatureThe mixture was refluxed for 17 h
  4. customcarefully quenched with an excess of 10% aqueous hydrochloric acid
  5. customThe THF was removed under vacuum
  6. extractionthe residue was extracted with three 50 mL aliquots of methylene chloride
  7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed
  10. customThe crude product was recrystallized from methylene chloride/pentane

Sources & evidence

ORD record
ord-e01606a0026d4463b5f5c69118422b29
Source dataset
uspto-grants-1993_04
Patent number
US05200544

Reaction notes

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