Utilization of hexabromoacetone for protection of alcohols and aldehydes and deprotection of acetals, ketals, and oximes under UV irradiation

• DOI: 10.1007/s11164-017-3168-0
• Publication Date: 2017-10-20T15:09:38Z
• Authors: Kittichai Chaiseeda; Ladawan Chantharadet; Warinthorn Chavasiri
• Keywords: 01 natural sciences; 0104 chemical sciences

Hexabromoacetone (HBA) was efficiently used for the protection of alcohols and aldehydes and deprotection of benzaldehyde dimethyl acetal, solketal, and other acetals and ketals. In only 10 min, the protection of glycerol yielded 90% of solketal and protection of benzaldehyde gave 95% of benzaldehyde dimethyl acetal. The deprotection of benzaldehyde dimethyl acetal under UV irradiation gave over 90% yield of benzaldehyde within 15 s using only 2.5 mol% of HBA. HBA was also successfully used for deoximation. Solvent was found to play an important role in the efficiency of HBA for these reactions.