http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-714371-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C2601-14 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C323-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-673 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-71 |
| filingDate | 1952-05-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1954-08-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-714371-A |
| titleOfInvention | Cyclohexylphenyl ketones |
| abstract | The invention comprises (1) compounds of the formula <FORM:0714371/IV (b)/1> where Y is hydroxy or acyloxy (not over 15 carbon atoms) and R is -COCH2Z or -CH2COCH2Z, Z being chlorine, bromine or iodine; (2) the following compounds when made by the processes described below: (a) Y = keto, Z = as in (1); (b) Y = hydroxy or acyloxy, Z = hydroxy or acetoxy; (c) Y = keto, Z = hydroxy. The compounds where R is -COCH2Z are made from acyloxycyclohexylbenzenes by Friedel-Craft condensation with a haloacetyl chloride or bromide to give p-(acetoxycyclohexyl) - phenacyl halides which on acid hydrolysis yield p-(hydroxycyclohexyl)-phenacyl halides, oxidized by chromic acid to (ketocyclohexyl) - phenacyl halides. The hydroxycyclohexyl and acetoxycyclohexyl compounds are converted into the corresponding phenacyl acetates by treatment with potassium acetate and the hydroxy compound can then be oxidized with chromic acid to p-(ketocyclohexyl)-phenacyl acetate. Finally all three phenacyl acetates are hydrolysed with potassium bicarbonate in aqueous methanol, yielding p - (acetoxy - cyclohexyl) - phenacyl alcohol, p-(hydroxycyclohexyl) - phenacyl alcohol and p-(ketocyclohexyl)-phenacyl alcohol. For the series where R is -CH2COZ, p-(acetoxycyclohexyl)-acetophenone is converted by the Willgerodt reaction into p-(acetoxycyclohexyl)-phenylacetic acid, re-acetylation being necessary, and the acid treated with thionyl chloride and diazomethane to give p-(acetoxycyclohexyl)-benzyl diazomethyl ketone. The latter gives (1) p - (acetoxycyclohexyl) - benzyl halomethyl ketone with ethereal hydrogen halide; (2) p - (acetoxycyclohexyl) - benzyl acetoxymethyl ketone with potassium acetate; and (3) p - (acetoxycyclohexyl) - benzyl hydroxymethyl ketone with dilute sulphuric acid. The halomethyl ketone is hydrolysed by alcoholic mineral acid to p-(hydroxycyclohexyl)-benzyl halomethyl ketone which with potassium acetate produces p-(hydroxycyclohexyl)-benzyl acetoxymethyl ketone. The two last named are oxidized with chromic acid to p-(ketocyclohexyl)-benzyl halomethyl ketone and p-(ketocyclohexyl) - benzyl acetoxymethyl ketone respectively. The acetoxymethyl compounds on treatment with potassium bicarbonate in aqueous methanol yield p-(hydroxycyclohexyl)-benzyl hydroxymethyl ketone and p-(ketocyclohexyl)-benzyl hydroxymethyl ketone. Examples are given of the above reactions. In each case the compounds where Z is iodine are made not directly but by treating their bromine analogues with sodium iodide. |
| priorityDate | 1951-05-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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