Phenaglycodol

Phenaglycodol

Clinical data
ATC code	None
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

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.

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, [4445-13-0] (5). Esterification to Ethyl p-chloroatrolactate [100126-96-3](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 [99-91-2] and acetone with magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol.

• See "Novel trifluoromethyl derivatives of substituted diols" U.S. Patent 3,134,819 also.
• A Pinacol rearrangement occurs in acidic water:

See also

• Metaglycodol
• Fenpentadiol