Hydrochloric Acid → 2-Nitrobenzyl alcohol

HRID 1854523Notes

Reaction equation

HRID 1854523 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=O)C.[OH-].[K+].Cl>O>[N+:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][OH:4])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 131771(2-Nitrophenyl)methyl acetate

Product 1

HCID 119232-Nitrobenzyl alcoholYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of compound 62 (70 mg, 0.18 mmol) in H2O (10 mL) was added 10% aq. KOH solution (0.5 mL). The reaction mixture was heated under reflux for 24 h. The reaction solution was cooled to r. t., and adjusted to pH 7 with 1 M HCl, then concentrated to half volume. The solution was kept at 0° C. for 2 h, and filtered. The crude precipitate was purified by silica gel column (elute hexane/EtOAc:1/1) to afford 63 (27 mg, 50%) as white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. temperatureThe reaction solution was cooled
  4. concentrationconcentrated to half volume
  5. filtrationfiltered
  6. customThe crude precipitate was purified by silica gel column (elute hexane/EtOAc:1/1)

Sources & evidence

ORD record
ord-5d180401fd3d4d32ac4032d0db2cfc49
Source dataset
uspto-grants-2015_02
Patent number
US08962670B2

Reaction notes

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