141-26-4

Usage

Uses

In soap perfumes; insect repellent.

InChI:InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h8,10H,1,4-7H2,2-3H3

Upstream product

• 34212-48-1 (R)-7-hydroxy-3,7-dimethyl-octanal 
• 18023-22-8 3,5-dimethylbenzenesulfinic acid 
• 5713-07-5 3,7-dimethyl-oct-7-en-1-ol 
• 106-22-9 Citronellol 
• 89-79-2 isopulegol 
• 124323-94-0 nitrate d'isopulegyle 

Downstream Products

• 925-69-9 (S)-6-methyl-octan-2-one 

Relevant academic research and scientific papers

Oxidizing polymers: A polymer-supported, recyclable hypervalent iodine(V) reagent for the efficient conversion of alcohols, carbonyl compounds, and unsaturated carbamates in solution

The oxidation of various alcohols and cyclization of an olefinic carbamate succeeds with the first polymer-supported iodine(v) reagent (see scheme). The novel oxidizing polymer oxidizes sensitive and complex alcohols, including protected amino alcohols, efficiency in good excellent yields. In addition, the α,β-dehydration of a ketone is demonstrated.

Reaction of isopulegol and similar alcohols with sulfuryl chloride

The reaction of isopulegol with sulfuryl chloride (or chlorine) gives two types of products: on one hand 8-chlorocitronellal and 6-chloroisocitronellal both issued from a fragmentation pathway and, on the other hand 10-chloroisopulegol resulting from an allylic chlorination.The first process, the radical nature of which is demonstrated, is clearly favored by elevated temperatures while the second one is exclusive at 0 deg C.Homologous compounds such as p-mentha-1,8-dien-5-ols, 3-phenylisopulegol and isopulegone dioxolane give rise to one or both of these processes. --- Key Words: allylic chlorination / radical fragmentation

FRAGMENTATION OF ISOPULEGOL BY A RADICAL PROCESS

The reaction of isopulegol with sulfuryl chloride leads in certain conditions to a mixture of 8-chloro citronellal and 6-chloro isocitronellal.The radical character of this fragmentation is supported by the result of two reactions known to proceed via an alkoxy radical.

OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES via aci-NITROESTERS OF ETHYL NITROACETATE UNDER NEUTRAL CONDITIONS

The reaction of alcohols with ethyl nitroacetate, diethyl azodicarboxylate, and triphenylphosphine gave the corresponding aldehydes or ketones in 52-85percent yields.