http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-797200-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_966a6c1f382ec9bcb5e3839dfd73e5b8 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C2601-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C2601-16 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C403-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C403-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-513 |
| filingDate | 1956-05-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1958-06-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-797200-A |
| titleOfInvention | Manufacture of unsaturated aldehydes |
| abstract | The invention comprises 4-[21,61,61-trimethyl cyclohexadien - (11,31) - yl - (11)] - 2 - methy - buten-(2)-al-(1) and a method of making it and also [2,6,6 - trimethyl - cyclohexen - (1) - yl-(1)]-acetaldehyde, [2,6,6 - trimethyl - cyclohexadien-(1,3) - yl - (11)] - acetaldehyde and 4 - [21,61,61-trimethyl - cyclohexen - (11) - yl - (11)] - 2 - methyl-buten - 2 - al - (1) by acetalising [2,6,6 - tri - methyl - cyclohexylidene - (1)] - acetaldehyde or 4 - [21,61,61 - trimethyl - cyclohexylidene - (11)]-2-methyl - buten - (2) - al - (1) or either of the corresponding compounds containing a double bond in 2,3-position of the cyclohexylidene radical by treating the same with a trialkyl ester of an orthoalkanoic acid in presence of an acid condensing agent, splitting off one mol. alcohol from the acetal so obtained by heating with an acidic agent in presence of a tertiary base to give an enol-ether, and hydrolysing the enol-ether under acid conditions. Orthoformic ethyl ester may be the orthoalkanoic ester, and acid condensing agents specified are boron trifluoride etherate, zinc chloride, ammonium nitrate, phosphoric acid, or p-toluene sulphonic acid. The splitting off of alcohol may be accomplished with phosphorus pentoxide, phosphorus oxychloride, or acetic anhydride in presence of an organic base. Examples describe (A) the acetalisation of each of the four starting materials with orthoformic ethyl ester in ethanol in presence of phosphoric acid to give 1,1 - diethoxy - 2 - [21,61,61 - trimethyl - cyclo-hexylidene - (11)] - ethane, 1,11 - diethoxy - 2 - [21,61,61 - trimethyl - cyclohexen - (21) - ylidene - (11)] - ethane, 1,1 - diethoxy - 4 - [21,61,61 - trimethyl - cyclohexylidene - (11)] - 2 - methyl-butene - (2), and 1,1 - diethoxy - 4 - [21,61,61 trimethyl - cyclohexen - (21) - ylidene - (11)] - 2 - methyl-butene-(2), (B) the treatment of these acetals with phosphorus oxychloride or acetic anhydride and pyridine in toluene (together with p-toluene-sulphonic acid when acetic anhydride is used) to give the enol-ethers 1 - ethoxy - 2 - [21,61,61 - trimethyl - cyclohexen - (11) - yl - 11] ethylene, 1 - ethoxy - 2 - [21,61,61 - trimethyl - cyclohexadien - (11,31) - yl - (11)]-ethylene, 1 - ethoxy - 4 - [21,61,61 - trimethyl-cyclohexen - (11) - yl - (11)] - 2 - methyl - buta-diene - 1,3, 1 - ethoxy - 4 - [21,61,61 - trimethyl-cyclohexadien - (11,31) - yl - (11)] - 2 - methyl-butadiene-(1,3), and (3) the hydrolysis of these enol-ethers with sulphuric, phosphoric, or p-toluene sulphonic acid in aqueous-alcoholic solution. [2,6,6 - Trimethyl - cyclohexylidene-(1)] - acetaldehyde and [2,6,6 - trimethyl-cyclohexen - (2) - ylidene - (1)] - acetaldehyde are prepared from 2,6,6-trimethyl-cyclohexanone and 2,6,6 - trimethyl - cyclohexen - (2) - one-(1) by condensation with b -chlorvinyl ether in liquid ammonia in presence of lithium, followed by hydrogenation. Alkyl radicals concerned above contain 1-6 carbon atoms. Specifications 773,863, 789,693 and 797,201 are referred to. |
| priorityDate | 1955-05-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 54.