Phenaglycodol

Phenaglycodol

Systematic (IUPAC) name
2-(4-chlorophenyl)-3-methyl-2,3-butanediol
Identifiers
CAS Number	79-93-6
ATC code	None
PubChem	CID: 6617
ChemSpider	6365
Chemical data
Formula	C11H15ClO2
Molecular mass	214.689 g/mol
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

Phenaglycodol (INN, BAN; 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 structurally and pharmacologically to meprobamate, though it is not a carbamate.

Synthesis

Jack Mills "2-chlorophenyl-3-methyl-2, 3-butanediols" U.S. Patent 2,812,363 (1957 to Eli Lilly Co.).

p-Chloroacetophenone and NaCN are reacted together to give the corresponding cyanohydrin (cf Strecker synthesis). The cyano group is then hydrated in acid to the corresponding amide, thus p-chloroatrolactamide (4) is formed. The amide group is then further hydrolyzed with a 2nd equivalent of water in concentrated lye to p-chloroatrolactic acid (5); this is then esterified to Ethyl p-chloroatrolactate (6). Finally, nucleophilic addition a couple of equivalents of MeMgI are added to the ester give Phenaglycodol (7) crystals.

Notes

• See "Novel trifluoromethyl derivatives of substituted diols" U.S. Patent 3,134,819 also.

See also

• Metaglycodol
• Fenpentadiol