Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 24
834
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Sodium Lauryl Sulfate–Catalyzed Oxidative Chlorination of Aromatic Compounds

, , &
Pages 3655-3663 | Received 21 Feb 2011, Published online: 20 Aug 2012
 

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

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.

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 422.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.