Phenaglycodol

{{Drugbox

| IUPAC_name = 2-(4-chlorophenyl)-3-methyl-2,3-butanediol

| image = Phenaglycodol.svg

| image_class = skin-invert-image

| CAS_number = 79-93-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = LMQ31KU50K

| ATC_prefix = None

| ATC_suffix =

| PubChem = 6617

| DrugBank =

| ChemSpiderID = 6365

| chemical_formula =

| C=11 | H=15 | Cl=1 | O=2

| SMILES = CC(C)(C(C)(c1ccc(cc1)Cl)O)O

| StdInChI = 1S/C11H15ClO2/c1-10(2,13)11(3,14)8-4-6-9(12)7-5-8/h4-7,13-14H,1-3H3

| StdInChIKey = HTYIXCKSEQQCJO-UHFFFAOYSA-N

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| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

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Phenaglycodol (brand names Acalmid, Acalo, Alterton, Atadiol, Felixyn, Neotran, Pausital, Remin, Sedapsin, Sinforil, Stesil, Ultran){{cite book| vauthors = Usdin E, Efron DH, ((U.S. National Institute of Mental Health)) |title=Psychotropic drugs and related compounds|url=https://books.google.com/books?id=t-dsAAAAMAAJ|year=1972|publisher=National Institute of Mental Health; [for sale by the Supt. of Docs., U.S. Govt. Print. Off., Washington|isbn=9780080255101}} is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties.{{cite book| vauthors = Vida J |title=Anticonvulsants|url=https://books.google.com/books?id=u-qOecoMmqMC&pg=PA578|date=19 July 2013|publisher=Elsevier|isbn=978-0-323-14395-0|pages=578–}}{{cite book| vauthors = Haddad LM, Winchester JF |title=Clinical Management of Poisoning and Drug Overdose|url=https://archive.org/details/clinicalmanageme00hadd|url-access=registration|year=1983|publisher=Saunders|isbn=978-0-7216-4447-9}} It is related pharmacologically to meprobamate, though it is not a carbamate.{{cite book| vauthors = Drill VA |title=Pharmacology in Medicine: A Collaborative Textbook|url=https://books.google.com/books?id=FfdsAAAAMAAJ|year=1958|publisher=McGraw-Hill}}{{cite book | vauthors = Beckman H |title=Pharmacology; the nature, action and use of drugs|url=https://books.google.com/books?id=i_5sAAAAMAAJ|year=1961|publisher=Saunders}}

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.{{cite patent | inventor = Mills J | title = 2-Chlorophenyl-3-methyl-2,3-butanediols | country = US | number = 2812363 | gdate = 5 November 1957 | assign = Eli Lilly Co. | url = https://patents.google.com/patent/US2812363A }}{{Cite patent|country=GB|number=788896|pubdate=1958-01-08|title=Improvements in or relating to novel substituted butanediol|assign1=Eli Lilly & Co.|inventor = Mills J }}

File:Phenaglycodol synthesis.svg

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.{{cite journal | doi = 10.1016/j.tetlet.2004.03.109 | title = Mg-promoted mixed pinacol coupling | date = 2004 | vauthors = Maekawa H, Yamamoto Y, Shimada H, Yonemura K, Nishiguchi I | journal = Tetrahedron Letters | volume = 45 | issue = 20 | pages = 3869–3872 }}

File:Phenaglycodol synthesis2.svg

Phenaglycodol

Synthesis

See also

References

Further reading