Tin tetrachloride → HCID 44139769, compound

HRID 1896984Notes

Reaction equation

HRID 1896984 reaction equation
[O:1]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-])=O)=[C:10]([CH3:18])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.Cl>[O:1]([C:8]1[CH:9]=[C:10]([CH3:18])[C:11](=[CH:12][C:13]=1[CH3:14])[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 685941194-Phenoxy-2,5-dimethylnitrobenzene

Product 1

HCID 44139769HCID 44139769, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 12.3 g (50 mmol) of 4-phenoxy-2,5-dimethylnitrobenzene in 150 ml of dioxane and 150 ml of hydrochloric acid was admixed at room temperature with 34.1 g (151 mmol) of tin chloride. After 10 h of stirring at room temperature, the mixture was neutralized with aqueous NaHCO3 solution and extracted repeatedly with dichloromethane. Drying of the combined organic phases over Na2SO4 and evaporation of the solvent gave 7.9 g (99.5% purity, 73.2% yield) of the product; log P(HCOOH)=1.92.

Workup

  1. extractionextracted repeatedly with dichloromethane
  2. dry with materialDrying of the combined organic phases over Na2SO4 and evaporation of the solvent
  3. customgave 7.9 g (99.5% purity, 73.2% yield) of the product

Sources & evidence

ORD record
ord-f67cdb9155454b4e92d2c05d19c75e4d
Source dataset
uspto-grants-2013_08
Patent number
US08519003B2

Reaction notes

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