Xue, Tong published the artcileResearch on an abnormal reaction of N-methyl-di(2-hydroxyethyl)amine, Formula: C10H15NO, the publication is Huaxue Tongbao (2015), 78(12), 1162-1165, database is CAplus.
In organic synthesis, methanesulfonyl chloride was often used to react with alc. to turn hydroxyl into a more active leaving group-methanesulfonyl. However, we had found that, when N-methyl-di(2-hydroxyethyl)amine reacted with methanesulfonyl chloride, its hydroxyl groups were both substituted by chlorine atoms. A series of designed experiments indicated that the key reason of this phenomenon was the generation of three-membered ring azonia ion transition state. The formation of this transition state must meet three requirements: there must two carbon atoms between the nitrogen atom and hydroxyl group, nitrogen atom must have sufficient electron cloud d. and the steric hindrance around nitrogen atom cannot be too high.
Huaxue Tongbao published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C4H10O2, Formula: C10H15NO.
Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts