135683-65-7

Upstream product

• 6169-06-8 (S)-2-Octanol 
• 538-75-0 dicyclohexyl-carbodiimide 

Downstream Products

• 39998-99-7 (R)-(-)-(1-Methylheptyl) phenyl ether 
• 5978-70-1 (R)-Octan-2-ol 
• 54739-11-6 (S)-(+)-(1-Methylheptyl) phenyl ether 
• 103481-63-6 (S)-(+)-4-(1-Methylheptyl)phenol 
• 135628-86-3 (S)-(+)-2-(1-Methylheptyl)phenol 
• 106760-31-0 (R)(-)-N,N'-dicyclohexyl-O-(1-methylheptyl)-isourea 

Relevant academic research and scientific papers

Inversion of configuration of alcohols with O-alkyl-N,N'-dicyclohexylisoureas

(S)-(+)-N,N'-Dicyclohexyl-O-(1-methylheptyl)isourea [(S)-2] reacts with acetic acid in cyclohexane to give (R)-(-)-(1-methylheptyl) acetate [(R)-3] with 100% inversion of configuration. Reaction of isourea (R)-2 with phenol proceeds also with inversion of configuration (99.8%) yielding (S)-(+)-(1-methylheptyl) phenyl ether [(S)-4] as the main product; optically active 2- and 4-(1-methylheptyl)phenols [(S)-5] and [(S)-6], respectively, are formed simultaneously. These byproducts, besides others resulting from hydride-shifts, document that the mechanism proceeds via the methylheptyl cation intermediate.