TITLE:
Facile, Direct Reaction of Benzaldehydes to 3-Arylprop-2-Enoic Acids and 3-Arylprop-2-Ynoic Acids in Aqueous Medium
AUTHORS:
Thies Thiemann, Mohamed W. Elshorbagy, Mostafa H. F. A. Salem, Siraj A. N. Ahmadani, Yosef Al-Jasem, Mariam Al Azani, Mazen A. M. Al-Sulaibi, Bassam Al-Hindawi
KEYWORDS:
Carboxylic Acids, Arylpropiolic Acids, Wittig Olefination, One Pot Reaction, Aqueous Reaction Medium, Dehydrobromination, Hydrolysis
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.6 No.2,
June
3,
2016
ABSTRACT: Wittig reactions of benzaldehydes, alkanals, and cycloalkanals as well as of acetophenones are carried out with alkoxycarbonyl methylidenetriphenylphosphoranes in 10 w% aqueous NaOH, where the cinnamates and alkenoates produced are hydrolysed in situ and the corresponding acids are obtained after mostly simple extractive work-up, often without employing organic solvents. Under the same conditions, benzaldehydes are reacted with alkoxycarbonyl bromomethy-lidenephosphorane to produce 3-arylprop-2-ynoic acids (arylpropiolic acids).