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

HRID 1529689Notes

Reaction equation

HRID 1529689 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-e25ca8bad05f48a49c5ace7f80ac47a2
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

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