499-99-0Relevant articles and documents
Tschugajew,Pokrowski
, (1908)
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
Sharma, S. D.,Sethi, A. S.,Bedi, Asha Lata,Aggarwal, R. C.
, p. 811 - 812 (2007/10/02)
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.