Hydrochloric Acid → 2-Nitro-5-(3-hydroxyphenylthio)-p-xylene

HRID 576480Notes

Reaction equation

HRID 576480 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N+:9]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15](Br)=[CH:14][C:13]=1[CH3:20])([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+].Cl>CN(C)C=O.O>[N+:9]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([S:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=2)=[CH:14][C:13]=1[CH3:20])([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 8258081-Bromo-2,5-dimethyl-4-nitrobenzeneHCID 27366133-Hydroxybenzenethiol

Product 1

HCID 665838602-Nitro-5-(3-hydroxyphenylthio)-p-xyleneYield 50.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 18.9 g of 3-mercaptophenol (0.150 moles), 32.9 g of 2-nitro-5-bromo-p-xylene (0.143 moles) and K2CO3 (0.143 moles) in 95 ml of N,N-dimethylformamide is stirred at room temperature for 2 hours. A solution of HCl at 10% is added under stirring; the mixture is diluted with H2O and extracted with ethyl acetate. The organic phase is washed again with water, anhydrified on sodium sulfate, filtered and evaporated. 20 g of solid product are obtained, which is used as such for the subsequent reaction.

Workup

  1. stirringunder stirring
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed again with water
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e429364762db4c338b73196e58fb53c4
Source dataset
uspto-grants-2015_05
Patent number
US09040457B2

Reaction notes

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