Phenaglycodol

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]

Phenaglycodol

Clinical data
ATC code	None
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1]
Identifiers
IUPAC name 2-(4-chlorophenyl)-3-methyl-2,3-butanediol
CAS Number	79-93-6
PubChem CID	6617
ChemSpider	6365
UNII	LMQ31KU50K
CompTox Dashboard (EPA)	DTXSID6023444
ECHA InfoCard	100.001.124
Chemical and physical data
Formula	C11H15ClO2
Molar mass	214.69 g·mol−1
3D 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,1-3H3 Key:HTYIXCKSEQQCJO-UHFFFAOYSA-N

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]

One-step method

See also

• Metaglycodol
• Fenpentadiol