Dimethyl Sulfoxide → Phenol, 5-chloro-2-nitro-

HRID 1105982Notes

Reaction equation

HRID 1105982 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CS(C)=[O:14].[OH-].[Na+]>O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([OH:14])[CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 118992,4-DichloronitrobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 11900Phenol, 5-chloro-2-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

192 g of 2,4-dichloronitrobenzene, 220 g of DMSO and 0.5 ml of the emulsifier specified in Example 1 are introduced into the reaction vessel. 160 g of 50% NaOH are added at 60° C. within 1 hour and the reaction mixture is stirred for 22 hours at 60° C. Subsequently 150 ml of water are added, the mixture is stirred until the temperature has cooled to 20° C. and the red sodium salt of 5-chloro-2-nitrophenol is suction-filtered and washed three times with 50 ml portions of water. The moist salt is added to 122 g of 30% HCl yielding 5-chloro-2-nitrophenol as an oil which is separated and dried in vacuo. The yield is 151.5 g of 5-chloro-2-nitrophenol (87% of the theory), m.p. 36.5° C. having a degree of purity of 100% according to gas chromatography.

Workup

  1. additionare introduced into the reaction vessel
  2. stirringthe mixture is stirred until the temperature
  3. temperaturehas cooled to 20° C.
  4. filtrationthe red sodium salt of 5-chloro-2-nitrophenol is suction-filtered
  5. washwashed three times with 50 ml portions of water
  6. additionThe moist salt is added to 122 g of 30% HCl

Sources & evidence

ORD record
ord-75d11b068ac44b6c9d7e7b2f635e6c0e
Source dataset
uspto-grants-1982_01
Patent number
US04310711

Reaction notes

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