kinoprene

Place syntheses below. The IUPAC name is prop-2-ynyl (//E,E//)-(//RS//)-3,7,11-trimethyldodeca-2,4-dienoate. We found some backgroud information on Kinoprene.

(E,E)-2-Propynyl 3,7,11-trimethyl-2,4-dodecadienoate (E,E)-3,7,11-Trimethyl-2,4-dodecadienoic acid 2-propynyl ester 2,4-Dodecadienoic acid, 3,7,11-trimethyl-, 2-propynyl ester 2,4-Dodecadienoic acid, 3,7,11-trimethyl-, 2-propynyl ester, (E,E)- 2,4-Dodecadienoic acid, 3,7,11-trimethyl-, 2-propynyl ester, (E,E)- (9CI) 2-Kinoprene 2-Propynyl (E,E)-3,7,11-trimethyl-2,4-dodecadienoate 2-Propynyl 3,7,11-trimethyl-2,4-dodecadienoate DODECA-2,4-DIENOIC ACID, 3,7,11-TRIMETHYL-, 2-PROPYNYL ESTER, (2E,4E)- Enstar Enstar IGR ENT 70531 Kinopren Kinoprene Kinoprene [ANSI] XR 777 ZR 777 ZR-777 ZR-777 5E ZR77 Information taken from: []
 * SYNONYMS/RELATED:**

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 * Properties ||
 * Molecular weight:276.4g/mol; Physical form:Amber liquid. Density:0.921; Flash point:40.5℃ (Tag closed cup); Vapour pressure:0.956 mPa (20℃ ); Solubility:In water 5.2 mg/l. Soluble in most organic solvents.; Stability:Stable on storage. ||
 * Molecular Formula: C18H28O2  ||
 * Molecular Structure:

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Okay.... with the help of tutoring and Chapter 22 (Wade) in our textbook, we were able to come up with the synthesis shown below. Our synthesis was a condensation of aldehyde reaction. At least one of the acid group is restored by NaOCH3. RCOOH is the cis isomer. DMF is a polar solvent. SOCL2 replaced the hydroxy from the RCOOH with the Cl. The esterification of OH (fisher esterificaition) was used in the final synthesis to show the relationship between the alcohol and the acid to form an ester. This is probably the most challenging molecule on this wiki. I am impressed that you found and used the claison type condensation between the carboxylic ester and the aldehyde. As you mention, it isn't covered until chapter 22. It is a picky point, and not covered until the second semester, but the Fisher esterification refers to cooking an alkohol and carboxylic acid together with acid catalysis. The esterification through the acid chloride is much more gentle and better in a case like this where you want to avoid reacting the double and triple bonds. If you put in a reterosynthesis (for an example see Ana Baird's post on the alkene) this synthesis will be complete. Bruce Bondurant Thank you! We will post our retrosynthesis



This looks good.

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