Phenaglycodol
Chemical compound
From Wikipedia, the free encyclopedia
Phenaglycodol (brand names Acalmid, Acalo, Alterton, Atadiol, Felixyn, Neotran, Pausital, Remin, Sedapsin, Sinforil, Stesil, Ultran)[2] is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties.[3][4] It is related pharmacologically to meprobamate, though it is not a carbamate.[5][6]
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| ECHA InfoCard | 100.001.124 |
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| Formula | C11H15ClO2 |
| Molar mass | 214.69 g·mol−1 |
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Synthesis
p-Chloroacetophenone and potassium cyanide (KCN) are reacted together via a Strecker reaction to give the corresponding cyanohydrin (3). The cyano group is then hydrated in acid to the corresponding amide, p-chloroatrolactamide (4). The amide group is then further hydrolyzed with a second equivalent of water in concentrated lye to give p-chloroatrolactic acid (5). Esterification then provides ethyl p-chloroatrolactate (6). Finally, nucleophilic addition with methylmagnesium iodide give phenaglycodol (7) crystals.[7][8]
In a second method, a mixed pinacol coupling reaction between para-chloroacetophenone and acetone that was catalyzed by magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol.[9]
