876-18-6

Upstream product

• 96154-45-9 3,7-dimethylocta-4,6-dien-1-ol 
• 79664-97-4 methyl (3R)-3,7-dimethyl-6-oxo-7-octenoate 
• 73374-55-7 methyl (3R)-6-hydroxy-3,7-dimethyl-7-octenoate 
• 88609-92-1 C₆H₁₁LiO 
• 906716-81-2 4-methyl-2-(thiophenyl)tetrahydropyran 
• 81925-86-2 3,7-dimethyl-5-(2'-methyl-2'-propenyl)-7-octen-1,5-diol 
• 81925-87-3 8-hydroxy-2,6-dimethyl-2-octen-4-one 
• 1121-84-2 4-methyl-tetrahydro-pyran-2-one 
• 88609-81-8 Dithiocarbonic acid S-methyl ester S-[(E)-2-methyl-3-((2R,4R)-4-methyl-tetrahydro-pyran-2-yl)-allyl] ester 
• 16122-01-3 3,7-Dimethyl-6-octene-1,5-diol 
• 79665-01-3 methyl (3R,5E)-3,7-dimethyl-5,7-octadienoate 
• 79731-38-7 (3R,5E)-3,7-dimethylocta-5,7-dien-1-ol 
• 19550-64-2 2,6-Dimethyl-1,5-heptadien-4-ol 
• 124727-44-2 4-Methoxymethoxy-2,6-dimethyl-hepta-1,5-diene 

Relevant academic research and scientific papers

Aluminium triflate catalysed cyclisation of unsaturated alcohols: novel synthesis of rose oxide and analogues

Aluminium trifluoromethanesulfonate was used as an efficient catalyst for the cycloisomerisation of several unsaturated alcohols into cyclic ethers such as rose oxide and some of its ether analogues.

Process for producing a rose oxide

An improved process for production of an isomer mixture of Z- and E-2-?2-Methyl-prop-1-en-1-yl-!-4-methyl-tetrahydropyran, more commonly known under the name cis- and trans-rose oxide, which as a rule contains at least 80% of the natural Z-isomers (cis-rose oxide) which are valuable in the perfume industry.

SYNTHESES OF TETRAHYDROPYRANS BY PPh3/CBr4 INDUCED CYCLIZATION OF ACETALS : APPLICATION TO A SYNTESIS OF ROSE OXIDE

Substituted tetrahydropyrans are prepared in good yields by PPh3/CBr4 induced cyclization of acetals.The utility of this new procedure is illustrated by the synthesis of cis-2-(methyl-1 propenyl)-4 methyltetrahydropyran (rose oxide).

173. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Preparation of 3-Hydroxypropyl and 4-Hydroxybutyl Propenyl Ketones from γ- and δ-Lactones. Synthesis of (+/-)-Rose Oxide

Starting from γ- and δ-lactones 1-3, a two-step preparation of 3-hydroxypropyl and 4-hydroxybutyl propenyl ketones 10-18 is described, involving as the key step the β-cleavage of the bis(homoallylic) potassium alkoxides 4a-9a.This novel methodology is illustrated by a short synthesis of (+/-)-rose oxide (20).

Electrooxidative Cleavage of Carbon-Carbon Linkages. 1. Preparation of Acylic Oxoalkanoates from 2-Hydroxy- and 2-Acetoxy-1-cycloalkanones and Cycloalkanone Enol Acetates

A methodology is described for the synthesis of acyclic oxoalkanoates 2 by electrooxidative cleavage of carbon-carbon linkages of 2-oxocycloalkan-1-ols 1 and cycloalkanone enol acetates 3.The electrolysis of 1 was carried out in a MeOH-LiClO4-(Pt) system at a constant applied voltage of 20 V by using a divided cell, giving 2 in 82-97 percent yields.On the other hand, 3 was electrolyzed in MeOH-AcOH (10:1)-LiClO4-(Pt) at 2-8 deg to give 2 in 72-79 percent yields.Electrolysis of 4-hydroxy-p-menth-8-ene afforded methyl (3R)-3,7-dimethyl-6-oxo-7-octenoate, a chiral synthetic block for the synthesis of (+)-rose oxide, in 84 percent yield.Similarly, the procedure could be applied to the preparation of methyl(+)-6-oxo-6,7-dihydrocitronellate from (+)-menthone enol acetate (74 percent) as well as 4-hydroxy-p-menthone (94 percent).Other lithium salts, i.e., LiBF4 and CF3CO2Li, can be used for the present purpose, but there are some difficulties in producing 2 with Et4NOTs and Et4NClO4.A plausible mechanism of the formation of 2 from 1 is also discussed.