Hydrochloric Acid → (4-Methoxy-3-nitrophenyl)methanol

HRID 1826096Notes

Reaction equation

HRID 1826096 reaction equation
B.O1CCCC1.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19].Cl>O1CCCC1>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 666404-Methoxy-3-nitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 4432413(4-Methoxy-3-nitrophenyl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere and cooling with ice, borane-tetrahydrofuran complex (1.00 mol/L, tetrahydrofuran solution, 100 mL, 100 mmol) was added dropwise to a solution of 4-methoxy-3-nitrobenzoic acid (15.3 g, 76.1 mmol) in anhydrous tetrahydrofuran (200 mL) under stirring. After completion of the dropwise addition, the mixture was allowed to stand overnight at room temperature. The reaction mixture was cooled with ice again and 6 mol/L hydrochloric acid (20 mL) was added dropwise. After stirring for 30 minutes, the mixture was concentrated under reduced pressure. The residue was poured into 1 L of ice water and, after stirring for 30 minutes, the precipitates produced were collected by filtration, washed with water and dried to afford 12.5 g (90%) of the title compound as pale yellow crystals.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperatureThe reaction mixture was cooled with ice again
  3. stirringAfter stirring for 30 minutes
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe residue was poured into 1 L of ice water
  6. stirringafter stirring for 30 minutes
  7. customthe precipitates produced
  8. filtrationwere collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-280c51d6feba4657b2c7f140e9154026
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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