http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-872846-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_14effe3850d2129f863b969dac4f1db8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C321-00 |
| filingDate | 1957-10-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1961-07-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-872846-A |
| titleOfInvention | Process for naphthalene thioglycollic acids |
| abstract | Naphthyl thioglycollic acids such as <FORM:0872846/IV (b)/1> and <FORM:0872846/IV (b)/2> are prepared by heating a naphthol or a lower ether of a naphthol with (1) thioglycollic acid or one of its esters, or (2) a salt of an S-ester of thiosulphuric acid of the formula MO-SO2-S-CH2-X (wherein M is a metal-ion and X is a carboxyl, carboxylic ester, carboxylic-amide or nitrile group), in the presence of an acid catalyst such as sodium bisulphate, p-toluene sulphonic acid, or an alkane sulphonic acid. In the case of the esters, amides and nitriles, the diluted reaction product is hydrolysed to the free carboxylic acid. In Example 1, thioglycollic acid and 1-naphthol are heated at 115 DEG C. in the presence of sodium bisulphate, under a nitrogen blanket, to give 1-naphthylthioglycollec acid. Example 2 relates to the preparation of 2-naphthylthioglycollic acid by heating 2-naphthol and thioglycollic acid in the presence of mixed alkane sulphonic acids. Example 3 relates to the preparation of naphthalene-1,5-bis-thioglycollic acid by heating 1,5-naphthalenediol with thioglycollic acid in the presence of p-toluene sulphonic acid. The same reaction may also be used to prepare 1 - naphthol - 5 - thioglycollic acid. Example 4 relates to the preparation of 2-naphthylthioglycollic acid by heating 2-methoxynaphthalene and thioglycollic acid in the presence of p-toluene sulphonic acid. In Example 5, ethyl thioglycollate is heated with 2-naphthol in the presence of mixed toluene sulphonic acids. The reaction mixture is then diluted with water; the insoluble product is isolated, re-slurried with water, made alkaline with caustic, and heated on a steam-bath until saponification is complete. The mixture is finally acidified to give 2-naphthylthioglycollic acid. In Example 6, sodium carboxymethyl thiosulphate and 2-naphthol are heated in the presence of p-toluene sulphonic acid; and the reaction-product is hydrolysed to yield 2-naphthylthioglycollic acid. Sodium carboxymethyl thiosulphate is prepared by reacting chloroacetic acid with sodium thiosulphate. Example 7 describes the preparation of crude sodium S-carbethoxymethyl thiosulphate, and its subsequent use in the preparation of 2-naphthylthioglycollic acid. Examples 8, 9 and 10 relate to the preparation of 2-naphthylthioglycollic acid from 2-naphthol and sodium S-carboxamidomethyl thiosulphate, sodium S-cyanomethyl thiosulphate, and sodium carboxdimethylamido-methyl thiosulphate, respectively. The Specification also makes mention of the following naphthalene starting materials:-5-carboxy-2-naphthol; 7-sulpho - 2 - naphthol; and 3 - methyl - 2 - naphthol. Intermediates may be prepared by the action of chloroacetonilide and chloroacetmorpholide on sodium thiosulphate. |
| priorityDate | 1956-11-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 54.