Hydrochloric Acid → 4-Tert-butyl-2-chloro-5-nitro-phenol

HRID 401325Notes

Reaction equation

HRID 401325 reaction equation
[OH-].[K+].C(=O)(OC)[O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][C:6]=1[Cl:18].Cl>CO>[C:14]([C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([OH:4])=[C:6]([Cl:18])[CH:7]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 574702314-Tert-butyl-2-chloro-5-nitrophenyl methyl carbonate

Product 1

HCID 574702324-Tert-butyl-2-chloro-5-nitro-phenolYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (10.1 g, 181 mmol) was added to 4-tert-butyl-2-chloro-5-nitrophenyl methyl carbonate (40.0 g, 139 mmol) in MeOH (100 mL). After 30 min, the reaction was acidified with 1N HCl and extracted with dichloromethane. The combined organic layers were combined, dried over Na2SO4 and concentrated under vacuum. The crude residue was purified by column chromatography (Pet. Ether/EtOAc, 30:1) to give 4-tert-butyl-2-chloro-5-nitro-phenol (23.0 g, 68% over 2 steps).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe crude residue was purified by column chromatography (Pet. Ether/EtOAc, 30:1)

Sources & evidence

ORD record
ord-6d3d97df28fb44828b65280fc15e9f65
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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