http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-583209-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_f447dd19e95d30abea12973773a2845d http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c91f1dc29a50c63553a90d0220e21aaa http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_2a099115dff2123eefb20f9e4201aa7e |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C43-2055 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C43-205 |
| filingDate | 1939-03-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1946-12-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-583209-A |
| titleOfInvention | Process for the preparation of hydroxylated derivaties of ª†,ª€-diphenyl-n-hexane |
| abstract | Hydroxylated derivatives of g ,d -diphenyl-hexane suitable for use as substitutes for the follicular hormone are prepared by condensing two molecules of esters, ethers or mixed alkoxy-alkyl ethers of a -halogenated-n-propyl hydroxybenzene in the presence of a metal having a dehalogenating action, and saponifying the condensation products to the free hydroxyl bodies. The reaction may be represented as <FORM:0583209/IV/1> where R and R1 are hydroxybenzene radicals, the OH radicals of which are protected by ester, ether or alkoxyalkyl groups, X is a halogen and M a metal such as sodium, potassium or the liquid alloy of the two. Thus, two molecules of anethol hydrobromide yield 4,41-dimethoxy-g ,d -diphenyl-n-hexane from which the corresponding hydroxy body may be obtained. Condensation of iso-sapol hydrobromide and anathole hydrobromide produces in addition to the two symmetrical substances 4-methoxy-31,41-methylene dihydroxy-g -d -diphenylhexane. The methyl ether of iso-eugenol hydrochloride (or propenyl-3-4-veratrol hydrochloride) yields 3,4,31,41-tetramethoxy-g -d -diphenylhexane. In example 1, anethol is stirred with aqueous saturated hydrobromic acid at 0 DEG C. and the methol hydrobromide diluted with benzene, decanted, washed with water and then with sodium bicarbonate and dried with sodium sulphate, followed by calcium chloride. The benzene solution is mixed with metallic sodium chips in a flask fitted with a reflux condenser, and allowed to stand for 24 hours at a temperature not above 48 DEG C. More sodium is then added and the mixture refluxed. The benzene is then evaporated, the residue dissolved in ether, washed with water, the ether evaporated and the residue vacuum distilled. The product distils at 190-240 DEG C. at 7 mms. Dissolved in petroleum ether this product may then be crystallised (M.P. 144 DEG C.). Demethylation with hydrobromic acid preferably containing acetic anhydride yields 4,41 - dihydroxy - diphenyl-n-hexane (M.P. 182 DEG C.). In example 2 a benzene solution of propenyl-3,4-veratrol hydrochloride is introduced into a flask containing benzene and liquid potassium-sodium alloy. The mixture is agitated and the temperature kept below 60 DEG C. After cooling, the benzene solution is decanted and purified to yield 3,4,31,41-tetramethoxy - g - d - diphenyl - n-hexane which after demethylation yields the corresponding hydroxy body. |
| priorityDate | 1939-03-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 47.