http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-728446-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_5d9f3ca41550d315642580237250c5b0 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D317-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D319-08 |
| filingDate | 1952-01-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1955-04-20-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-728446-A |
| titleOfInvention | Improvements in synthesis of terpenoid materials |
| abstract | The invention comprises a ketal of the general formula <FORM:0728446/IV (b)/1> wherein X is a halogen atom and R11 is an alkylene radical, and the preparation thereof by reacting a 5-halo-2-pentanone with either an alkylene glycol or an alkyl orthoformate. Said ketal may be reacted with an active metal, e.g. Mg, Zn, Cd or Hg, to form an organohalometallic compound of the formula <FORM:0728446/IV (b)/2> or <FORM:0728446/IV (b)/3> wherein M is the active metal, or with lithium. The organohalometallic compound reacts with an aldehyde or ketone of the formula <FORM:0728446/IV (b)/4> where R is a hydrocarbon radical and R1 is either hydrogen or a hydrocarbon radical to form a carbinol of the formula <FORM:0728446/IV (b)/5> which can be dehydrated with an acid dehydrating agent, e.g. oxalic acid, p-toluenesulphonic acid, acetic anhydride, zinc chloride, phosphorus trichloride, oxalyl chloride and phosphorus oxychloride, to form the compound <FORM:0728446/IV (b)/6> or <FORM:0728446/IV (b)/7> p which upon hydrolysis with aqueous acid yields the unsaturated ketone <FORM:0728446/IV (b)/8> which upon hydrogenation yields the saturated ketone <FORM:0728446/IV (b)/9> As the alkylene glycol there may be used ethylene glycol, propylene glycol or butylene glycol, whilst the carbonyl compound may be pseudo-ionone, dimethyl ketone or methylheptenone. The reaction of the ketal with the active metal is effected in the presence of methyl iodide. The hydrogenation reaction may be effected in the presence of Raney nickel, platinum oxide or palladium. 5-Halo-2-pentanones are obtained by reacting an alkaline metal derivative of ethyl acetoacetate with ethylene oxide gas to form a -acetobutyrolactone which is reacted with hydrogen halide. |
| priorityDate | 1951-01-05-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
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