Sulfuric Acid → 2-Chloro-1,3,5-trimethylbenzene

HRID 2417346Notes

Reaction equation

HRID 2417346 reaction equation
[C:1]1([CH3:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[Cl-:10].[Na+].S(=O)(=O)(O)O.I([O-])(=O)(=O)=O.[Na+]>C(#N)C.O>[Cl:10][C:2]1[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=1[CH3:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 7947MesityleneHCID 23667635Sodium periodate

Product 1

HCID 154622-Chloro-1,3,5-trimethylbenzeneYield 40%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

Mesitylene (1 mmol) was treated with sodium chloride (1.2 mmol) in acetonitrile: water (2:1, 6 ml). 20% Sulfuric acid (5 ml) and sodium periodate (20 mol %) was added to the reaction mixture. The mixture was heated at 80° C. under inert atmosphere for 6 h. The product was purified by column chromatography to give chloromesitylene (40%).

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-cd9136772e4e4287b758710420331817
Source dataset
uspto-grants-2004_11
Patent number
US06825383B1

Reaction notes

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