Sulfuryl chloride → 2-Chloro-4-ethylphenol

HRID 1070468Notes

Reaction equation

HRID 1070468 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[CH3:2].S(Cl)([Cl:13])(=O)=O>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Cl:13][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 312424-Ethylphenol

Product 1

HCID 293552-Chloro-4-ethylphenolYield 77%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-ethylphenol (25.4 g, 0.21 mol) and sulfuryl chloride (18.5 ml, 0.23 mol) in carbon tetrachloride (40 ml) was stirred under heating at 70° C. for 3 hr. The reaction mixture was diluted with chloroform and washed with water. The organic layer was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 2-chloro-4-ethylphenol (25.1 g, 77%).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-2ed30d196fd74820ad28290ea3f1bf9b
Source dataset
uspto-grants-2005_06
Patent number
US06903094B2

Reaction notes

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