One-Pot O2-Oxidation and the Horner-Wadsworth-Emmons Reaction of Primary Alcohols for the Synthesis of (Z)-α,β-Unsaturated Esters was written by Ando, Kaori;Takaba, Chika;Kodama, Masahiro. And the article was included in Journal of Organic Chemistry in 2022.Name: (4-Chlorophenyl)methanol This article mentions the following:
Authors developed one-pot oxidation/olefination procedures of primary alcs. giving Z-α,β-unsaturated esters. TEMPO-(CuCl or CuBr2)-(2,2′-bipyridine) (1:1:1) catalyzed O2 oxidation of primary alcs. in the presence of Z-selective Horner-Wadsworth-Emmons reagent and K3PO4 or NaH gave Z-α,β-unsaturated esters with Z/E = 84:16 to 96:4 in high yields. A stepwise reaction was also developed. After TEMPO-CuBr2-(2,2′-bipyridine)-K3PO4 (1:1:1:1) catalyzed O2 oxidation of alcs. in MeCN, the resulting mixture was treated with a THF solution of Horner-Wadsworth-Emmons reagent and t-BuOK at -78°C to 0°C, giving Z-α,β-unsaturated esters with higher selectivity (Z/E = 91:9 to 99:1). In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7Name: (4-Chlorophenyl)methanol).
(4-Chlorophenyl)methanol (cas: 873-76-7) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Name: (4-Chlorophenyl)methanol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts