Haworth phenanthrene synthesis

Written by J.A Dobado | Last Updated on May 2, 2024

What is Haworth phenanthrene synthesis?

The Haworth phenanthrene synthesis is a multi-step process used to prepare phenanthrenes from naphthalenes. The process involves several key steps, including Friedel-Crafts acylation, as well as two Clemmensen reductions or Wolff-Kishner reductions. These reactions work together to transform naphthalene into phenanthrene, which can then be utilized in a variety of industrial applications.

References

• Haworth, R.D; “145. Syntheses of alkylphenanthrenes. Part I. 1-, 2-, 3-, and 4-Methylphenanthrenes” J. Chem. Soc., 1932, 1125-1133
  DOI: 10.1039/JR9320001125
• Haworth, R.D; “407. Synthesis of alkylphenanthrenes. Part IV. 7-Methyl-1-ethyl- and 1-ethyl-7-isopropyl-phenanthrenes : constitution of abietic and d-pimaric acids“. Chem. Soc., 1932, 2717-2720
  DOI: 10.1039/JR9320002717
• Robert Downs Haworth, Barnet Mark Letsky and Cecil Robert Mavin; “240. Syntheses of alkylphenanthrenes. Part II. Pimanthrene, 1 : 4 : 7-trimethylphenanthrene, retene, and 1 : 4-dimethyl-7-isopropylphen-anthrene” J. Chem. Soc., 1932, 1784-1792
  DOI: 10.1039/JR9320001784
• Robert Downs Haworth and Cecil Robert Mavin; “408. Synthesis of alkylphenanthrenes. Part V. 9-Methyl-, 1 : 9-dimethyl-, and 1 : 2 : 8-trimethyl-phenanthrenes” J. Chem. Soc., 1932, 2720-2723
  DOI: 10.1039/JR9320002720
• Robert Downs Haworth, Cecil Robert Mavin and George Sheldrick; “106. Synthesis of alkylphenanthrenes. Part VI. Attempts to synthesise the hydrocarbon “C₁₆H₁₄” derived from strophanthidin” J. Chem. Soc., 1934, 454-461
  DOI: 10.1039/JR9340000454