Sulfuric Acid → 2-Chloroanisole

HRID 2417344Notes

Reaction equation

HRID 2417344 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-:9].[Na+].S(=O)(=O)(O)O.I([O-])(=O)(=O)=O.[Na+]>C(#N)C.O>[Cl:9][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[O:7][CH3:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 7519AnisoleHCID 23667635Sodium periodate

Product 1

HCID 130112-ChloroanisoleYield 2%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
80 °C

Procedure

Anisole (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 reaction mixture. The mixture was heated at 80° C. under inert atmosphere for 4 h. The product was purified by column chromatography to give 4-chloroanosole (25%) and 2-chloroanisole (2%).

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-5b59aba41839419fae383e121005255d
Source dataset
uspto-grants-2004_11
Patent number
US06825383B1

Reaction notes

Loading…