Dichloromethane → Phenol, 2-chloro-3-nitro-

HRID 36865

Reaction equation

HRID 36865 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:11]([O-])(=O)=O.[K+].ClCCl>Cl.O>[Cl:11][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:10]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 111373-NitrophenolHCID 6426889Potassium Chlorate

Product 1

HCID 3013917Phenol, 2-chloro-3-nitro-Yield 64.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

73 g (0.52 mol) of 3-nitrophenol are dissolved in 2 liters-of 6N hydrochloric acid while heating. The mixture is cooled in an ice bath to 28°-30° C. 32 g (0.26 mol) of potassium chlorate in 500 ml of water are added over 1.5 hours and then, at the end of the addition, the mixture is left stirring for 30 minutes at 28°-30° C. The mixture is cooled to 15° C. and 1 liter of dichloromethane is added. The layers are separated and the organic phase is washed with water. The organic phase is dried and evaporated. The residue is purified by chromatography on a column of silica gel, eluting with a dichloromethane/methanol (80/20) mixture. Recrystallization is carried out from toluene. 29 g of product are obtained.

Workup

  1. temperaturewhile heating
  2. temperatureThe mixture is cooled in an ice bath to 28°-30° C
  3. additionat the end of the addition
  4. waitthe mixture is left
  5. customThe layers are separated
  6. washthe organic phase is washed with water
  7. customThe organic phase is dried
  8. customevaporated
  9. customThe residue is purified by chromatography on a column of silica gel
  10. washeluting with a dichloromethane/methanol (80/20) mixture
  11. customRecrystallization

Sources & evidence

ORD record
ord-945c0e5684024f81beb47d87c2e71169
Source dataset
uspto-grants-1995_05
Patent number
US05418241

Linked notes

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