Ethyl Acetate → 2-Chloro-5-nitrophenol

HRID 887654Notes

Reaction equation

HRID 887654 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])C=C[C:3]=1OC.[Cl-:13].[NH+]1C=CC=CC=1.CCO[C:23]([CH3:25])=[O:24]>Cl>[Cl:13][C:3]1[CH:2]=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:25][C:23]=1[OH:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 210272-Chloro-4-nitroanisoleHCID 69401Einecs 211-027-4

Product 1

HCID 692642-Chloro-5-nitrophenol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-chloro-4-nitroanisole (10 g, 53.3 mmol) and pyridinium chloride (50 g, 426 mmol) was heated at 200° C. for 3 h. After cooling to RT, the mixture was dissolved in 150 mL of aqueous 2N HCl and 150 mL of EtOAc. The organic phase was separated and was washed with aqueous 2N HCl (2×100 mL). The resulting organic phase was dried over MgSO4 and concentrated in vacuo. The title compound was obtained via chromatography (silica gel, 10:1 hexane/EtOAc) as a yellow solid.

Workup

  1. temperatureAfter cooling to RT
  2. customThe organic phase was separated
  3. washwas washed with aqueous 2N HCl (2×100 mL)
  4. dry with materialThe resulting organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ddad79046047424fb9c68dbf3df087d2
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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