phenaglycodol phenaglycodol phenaglycodol (brand names acalmid, acalo, alterton, atadiol, felixyn, neotran, pausital, remin, sedapsin, sinforil, stesil, ultran) is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties. it is related pharmacologically to meprobamate, though it is not a carbamate. phenaglycodolclinical dataatc codenoneidentifiers iupac name 2-(4-chlorophenyl)-3-methyl-2,3-butanediol cas number79-93-6pubchem cid6617chemspider6365uniilmq31ku50kcomptox dashboard (epa)dtxsid6023444 echa infocard100.001.124 chemical and physical dataformulac11h15clo2molar mass214.69 g·mol−13d model (jsmol)interactive image smiles cc(c)(c(c)(c1ccc(cc1)cl)o)o inchi inchi=1s/c11h15clo2/c1-10(2,13)11(3,14)8-4-6-9(12)7-5-8/h4-7,13-14h,1-3h3key:htyixckseqqcjo-uhfffaoysa-n synthesis patents:. p-chloroacetophenone and nacn are reacted together to give the corresponding cyanohydrin (cf strecker synthesis), cid:12439573. the cyano group is then hydrated in acid to the corresponding amide, p-chloroatrolactamide, cid:15255544 (4). the amide group is then further hydrolyzed with a 2nd equivalent of water in concentrated lye to p-chloroatrolactic acid, (5). esterification to ethyl p-chloroatrolactate (6). finally, nucleophilic addition a couple of equivalents of memgi are added to the ester give phenaglycodol (7) crystals. 40% one-step method: a mixed pinacol coupling rxn between 4-chloroacetophenone and acetone with magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol. notes see "novel trifluoromethyl derivatives of substituted diols" u.s. patent 3,134,819 also. a pinacol rearrangement occurs in acidic water: