3,4-Dinitrobenzoic acid → 3,4-Dinitrobenzyl alcohol

HRID 2250184Notes

Reaction equation

HRID 2250184 reaction equation
B.O1CCCC1.[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13](O)=[O:14])([O-:9])=[O:8]>O1CCCC1>[N+:7]([C:10]1[CH:11]=[C:12]([CH2:13][OH:14])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 107093,4-Dinitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 1573023,4-Dinitrobenzyl alcoholYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Borane-tetrahydrofuran complex (1M in tetrahydrofuran, 800 mL, 800 mmol) was added at −20° C. over 45 min to a solution of 3,4-dinitrobenzoic acid (93.5 g, 441 mmol) in tetrahydrofuran (300 mL). The resulting mixture was stirred at −20° C. for 1 h and then warmed to room temperature and stirred overnight. It was quenched by the addition of 32 mL of 1:1 acetic acid/water. Solvents were removed in vacuo and the residue was poured into an ice-cold 1000 mL of sat. sodium bicarbonate with vigorous stirring over 15 min. The mixture was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with sat. sodium bicarbonate, brine and dried over sodium sulfate. After filtration, solvents were removed to afford the title compound as a light yellow solid (100%). 1H-NMR (CDCl3, 500 MHz) δ 7.91 (d, J=8.0 Hz, 1H), 7.89 (s, 1H), 7.71 (dd, J=8.5, 1.0 Hz, 1H), 4.87 (s, 2H), 2.30 (s, 1H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. customIt was quenched by the addition of 32 mL of 1:1 acetic acid/water
  4. customSolvents were removed in vacuo
  5. additionthe residue was poured into an ice-cold 1000 mL of sat. sodium bicarbonate
  6. stirringwith vigorous stirring over 15 min
  7. extractionThe mixture was extracted with ethyl acetate (3×500 mL)
  8. washThe combined organic layers were washed with sat. sodium bicarbonate, brine
  9. dry with materialdried over sodium sulfate
  10. filtrationAfter filtration, solvents
  11. customwere removed

Sources & evidence

ORD record
ord-e4942b46788d44a195f44becb3dc4316
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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