Hydrochloric Acid → 4-Chloro-3-methylphenol

HRID 1741544Notes

Reaction equation

HRID 1741544 reaction equation
Cl.[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([OH:10])=[C:5]([N+]([O-])=O)[CH:4]=1>O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([OH:10])=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 235324-Chloro-5-methyl-2-nitrophenol

Product 1

HCID 17324-Chloro-3-methylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 160 ml of methanol, there were added 37.9 g of the 4'-chloro-5'-methyl-2'-nitrophenyl methanesulfonate as obtained in the above (ii) and 80 ml of a 7N aqueous solution of sodium hydroxide, followed by heating under reflux for 20 minutes. After cooling, the reaction mixture was poured into 500 ml of water and neutralized with hydrochloric acid. The crystals thus precipitated were filtered and recrystallized from acetone to give thereby 10.4 g (55 mmol) of 4-chloro-5-methyl-2-nitrophenol as yellow crystals. The yield from 4-chloro-3-methylphenol was 31%.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 20 minutes
  3. temperatureAfter cooling
  4. customThe crystals thus precipitated
  5. filtrationwere filtered
  6. customrecrystallized from acetone
  7. customto give

Sources & evidence

ORD record
ord-c3da07452a344e0887de799fe374ba28
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Reaction notes

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