meparfynol

Joseph: This is another great synthesis, Write up a brief description, and I think you have this one nailed as well. Bruce Bondurant JOSEPH WILLIAMS THIS SYNTHESIS IS DESCRIBES HOW MEPARFYNOL IF MADE FRON SCATCH USING TRIPLE BONDED CARDON SHORT CHAINS. IN THE REACTION WE USE SODIUM AMINE IN THE PRESENCE OF THE H2C2 TO PROTONATE THE H ATOM AND MAKE A H3C2 AND 1-BUTYNE. THIS REPRESENT THE FIRLST REACTION THAT TAKES PLACE IN THE SYNTHESIS OF MARPAFYNOL. WE ALSO ADD HGSO4 ADN H2SO4 TO MAKE AND ALCOHOL AND A KETONE OUT OF IT. THE THIRD REACTION INCLUDES THE ADDTION OF NANH2 TO MAKE AN ACYTALIDE ION AS DISCUSSED IN CLASS B DR BONDURANT AND WE DO THIS IN THE PRESENCE OF TOULENE IF AVAILABLE. THE NA ION THEN REACTS WITH THE H2C2. THE FINAL PRODUCT OF THEN MARPAFYNOL.

**Additional Names:** ethyl ethynyl methyl carbinol; 2-ethynyl-2-butanol; methylparafynol; methylpentynol
==== **Trademarks:** Allotropal (Heyl); Anti-Stress (Sintyal); Apridol; Atemorin; Atempol (Norgine); Dalgol; Dorison; Dormalest; Dormidin; Dormigen; Dormiphen; Dormison (Schering); Dormosan; Formison; Hesofen; Hexofen; Imnudorm; Oblivon; Pentadorm; Perlopal; Riposon; Seral; Somnesin (Central Pharm.) ====

**Percent Composition:** C 73.43%, H 10.27%, O 16.30%
==== **Literature References:** Prepd from methyl ethyl ketone and sodium acetylide in liquid ammonia or by a Grignard reaction: **DE** **285770** (1913 to Bayer); also **DE** **289800** and **DE** **291185** //see// //Frdl.// **12,** 55, 56, 57; Sung Wouseng, //Ann. Chim.// [10] **1,** 343 (1924); Rupe, Vonaesch, //Ann.// **442,** 80 (1925); Carothers, Coffman, //J. Am. Chem. Soc.// **54,** 4071 (1932); Campbell //et al.,// //ibid.// **60,** 2882 (1938); Campbell, Campbell, //Proc. Indiana Acad.// ====

**Percent Composition:** C 59.56%, H 7.85%, N 9.92%, O 22.67%
==== **Literature References:** Prepn: McLamore //et al.,// //J. Org. Chem.// **20,** 1379 (1955); from 3-methyl-1-pentyn-3-ol, trichloroacetic acid, KOCN: McCrea //et al.,// **GB** **761817** (1956 to British Schering). Acute toxicity: Soehring //et al.,// //Arzneim.-Forsch.// **5,** 161 (1955). ==== ==== **Properties:** Crystals from ether + petr ether. mp 55.8-57° (McLamore); from cyclohexane, mp 53.5-55° (McCrea). bp 16 120-121°; bp 0.01 95°. Solubility in water: 1.6 g/100 ml. LD 50 (4 hr) s.c. in mice: 0.56 g/kg (Soehring). ====

THIS SYNTHESIS IS ALSO RFLECTED IN WADES ORGANIC CHEMISTRY BOOK CHANPTER 10 AND FROM ORGANIC CHEMISTRY. COM,/// JOSEPH WILLIAMS ( EXTRA CREDIT)//
==== //Sandra Zivkovic Resources: Winter, Arthur. // Organic Chemistry I for Dummies //. Indianapolis: Wiley. Hathaway, Bruce A.// Organic Chemistry: The Easy Way //. Hauppauge: Barron's Educational Series, 2005. Wade: Mechanism chapters and notes from class ====