499-99-0

Upstream product

• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 22567-21-1 (1S,2S,5S)-5-isopropenyl-2-methylcyclohexan-1-ol 
• 19876-42-7 1-(4-methyl-cyclohex-2-enyl)-ethanone 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 63543-28-2 Isopulegon Tosylhydrazon 
• 57610-48-7 prop-2-(4'-methyl-2'-cyclohexen-1'-yl)-2-en-1-ol 
• 70424-76-9 trans-2-hydroxymethyl-3-carene 
• 19876-37-0 1-[(Z)-2-(4-Methyl-cyclohex-2-enyl)-vinyl]-piperidine 
• 19876-38-1 4-Methyl-cyclohex-2-enecarbaldehyde 
• 19876-40-5 4-methylcyclohex-2-ene-1-carboxylic acid 
• 19876-41-6 4-Methyl-cyclohex-2-enecarbonyl chloride 

Downstream Products

• 58718-55-1 3,5-dimethyl-5-(4-methyl-cyclohex-3-enyl)-4,5-dihydro-isoxazole 
• 99-82-1 Menthane 
• 877467-48-6 trans-p-menth-2-en-9-ol 
• 19876-42-7 1-(4-methyl-cyclohex-2-enyl)-ethanone 
• 64-19-7 acetic acid 
• 874533-94-5 2,3,8,9-tetrabromo-p-menthane 

Relevant academic research and scientific papers

2-CARENE IN THE PRINS REACTION

The Prins reaction of 2-carene with formaldehyde has been studied.The main reaction product is 2-hydroxymethyl-3-carene.The dehydration of 2-hydroxymethyl-3-carene is accompanied by a skeletal rearrangement of the carane structure with the formation of products having a seven-membered ring.

Synthesis of 5,5-Ethylenedioxy-2-methylhept-2-en-1-ol, a Key Intermediate for Synthesis of dl-Carvone and a New Synthesis of Isolimonene

Ethylene ketal (IV) of 3-ketopentanoate (III) on reduction with LAH in dry ether gives the alcohol (V) which on oxidation with pyridinium chlorochromate affords 3,3-ethylenedioxypentanal (VI).Reaction of VI with ethyl α-diethylphosphonopropionate in THF yields ethyl 5,5-ethylenedioxy-2-hept-2-eneoate (VII).Reduction of VII with LAH in benzene provides the title alcohol (VIII).Synthesis of dl-isolimonene (II) has been accomplished by submitting prop- 2-(4'-methyl-2'-cyclohexen-1'-yl)-2-en-1-ol (IX) to hydrogenolysis reaction with Na/ethanol in liquid ammonia.