Sodium Lauryl Sulfate–Catalyzed Oxidative Chlorination of Aromatic Compounds

Abstract

Chlorination of commercially important aromatic compounds using sodium chloride as chlorine source and sodium periodate as oxidant in acidic medium catalyzed by sodium lauryl sulfate (SLS) led to the chloro-substituted aromatics in good yields and purity. Addition of sodium lauryl sulfate led to increased chlorination rate, better yield, excellent purity, and better quality of end product. The advantages of the present method are greater yield, excellent purity, and shorter reaction time at room temperature. Also dichlorinated product can be obtained by increasing the amount of sodium chloride and sodium periodate at slightly higher temperature (40 °C).

GRAPHICAL ABSTRACT

Keywords:

• Chlorination
• chloroarenes
• regioselectivity
• sodium lauryl sulfate
• sodium periodate

ACKNOWLEDGMENTS

The authors express their thanks to Kapil Kumar, SRF Ltd., and the director, Sophisticated Analytical Instrumentation Facility, Punjab University, Chandigarh, for carrying out the spectral analysis of the compounds.

Notes

^a Reaction conditions: substrate, 0.01 mol; NaCl, 0.03 mol; NaIO₄, 0.005 mol; AcOH, 10 mL; H₂SO₄, 1.0 mL; SLS, 50 mg; temp 25 °C.

^b Reaction conditions: substrate, 0.01 mol; NaCl, 0.05 mol; NaIO₄, 0.01 mol; AcOH, 10 mL; H₂SO₄, 1.0 mL; SLS, 50 mg; temp 40 °C.

^a Isolated yield.

^b Purity determined by HPLC.

^c Reaction conditions: substrate, 0.01 mol; NaCl, 0.03 mol; NaIO₄, 0.005 mol; AcOH, 10 mL; H₂SO₄, 1.0 mL; SLS, 50 mg; temp 25 °C.

^d Reaction conditions: substrate, 0.01 mol; NaCl, 0.05 mol; NaIO₄, 0.01 mol; AcOH, 10 mL; H₂SO₄, 1.0 mL; SLS, 50 mg; temp 40 °C.

Notes. Reaction conditions: substrate, 0.01 mol; NaIO₄, 0.005 mol; AcOH, 10 mL; H₂SO₄, 1.0 mL; SLS, 50 mg; temp 25 °C.

Notes. Reaction conditions: substrate, 0.01 mol; NaCl, 0.03 mol; AcOH, 10 mL; H₂SO₄, 1.0 mL; SLS, 50 mg; temp 25 °C.

Notes. Reaction conditions: substrate, 0.01 mol; NaCl, 0.03 mol; NaIO₄, 0.005 mol; AcOH 10 mL; H₂SO₄ 1.0 mL; temp 25 °C.

^a Isolated yield.

^b Purity determined by HPLC.

Notes. Reaction conditions: substrate, 0.01 mol; NaCl, 0.03 mol; NaIO₄, 0.005 mol; AcOH, 10 mL; H₂SO₄, 1.0 mL; SLS, 50 mg; temp 25 °C.