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Subject: Re: [DCHAS-L] Experience with 4-methylcyclohexene Lab
Date: Thursday, November 1, 2018 at 11:29:55 AM
Author: David C. Finster <dfinster**At_Symbol_Here**WITTENBERG.EDU> 		Next by Date:
Subject: [DCHAS-L] Chemical Safety headlines (13 articles)
Date: Fri, 2 Nov 2018 07:03:28 -0400
Author: Ralph Stuart

From: Mark Bachrach <markbachrach2015**At_Symbol_Here**U.NORTHWESTERN.EDU>
Subject: Re: [DCHAS-L] Experience with 4-methylcyclohexene Lab
Date: Thu, 1 Nov 2018 15:50:38 -0400
Reply-To: ACS Division of Chemical Health and Safety <DCHAS-L**At_Symbol_Here**PRINCETON.EDU>
Message-ID: CADv-0JbVX0eoVmz4kJ3sX0wXgszWnVd37xiutjJwWvLv4r3KoQ**At_Symbol_Here**mail.gmail.com
In-Reply-To


I am not familiar with that lab procedure but have done a somewhat similar dehydration with iodine based on the paper by Kukovinets OS, Yamansarova ET, Kasradze VG, Lozhkina EA, Zainullin RA, Abdullin MI (2005) Russ J Org Chem 41:673.

1-Methylcyclohexene (X) was prepared by treating with 8.33 g (0.085 mol) of cyclohexanone the Grignard reagent obtained from 14.2 g (0.10 mol) of methyl iodide and 2.4 g (0.10 mol) of Mg in 50 ml of anhydrous ethyl ether followed by reaction of the alcohol formed with iodine (5.4 g, 0.43 mol). Cycloolefin X was isolated similarly to compound VIII. Yield 7.75 g (95%), bp 106108 =B0C (15 mm Hg), nD 20 1.4304.

On Thu, Nov 1, 2018 at 12:11 PM David C. Finster <dfinster**At_Symbol_Here**wittenberg.edu> wrote:
Monique,

Here is a comment from my organic colleague:

"We do the lab with 2-methylcyclohexanol and use Amberlyst 15 ion exchange resin instead of a H2SO4 or H3PO4. We did this lab yesterday in fact and it appeared to work well. The alkene products do smell, so keeping it in the hood helps."

Dave


David C. Finster
Professor, Department of Chemistry
Wittenberg University
937-327-6441
https://www.wittenberg.edu/academics/chemistry/facultystaff/finster2.html


-----Original Message-----
From: ACS Division of Chemical Health and Safety [mailto:DCHAS-L**At_Symbol_Here**PRINCETON.EDU] On Behalf Of Wilhelm, Monique
Sent: Wednesday, October 31, 2018 1:15 PM
To: DCHAS-L**At_Symbol_Here**PRINCETON.EDU
Subject: [DCHAS-L] Experience with 4-methylcyclohexene Lab

Hi everyone,

I am reaching out to see if anyone has experience with the dehydration of 4-methylcyclohexanol to 4-methylcyclohexene lab in the Pavia et al lab textbook. The reaction seems to call for an awful lot of H2SO4 in addition to H3PO4 and is giving off several noxious odors. I would like to recommend getting rid of the H2SO4 but am concerned about whether this may cause unwanted organophosphates to be produced. I am concerned as I cannot figure out what kind of byproduct or decomp products we may be getting.

Does anyone have any thoughts on this? I am not an organic chemist, so maybe I am just overthinking this one too much.


Monique
_________________________________________________________
Monique Wilhelm, M.S., NRCC Certified CHO ACS CHAS Secretary|2017 CERM E. Ann Nalley Award Recipient Laboratory Manager|Adjunct Lecturer|Chemistry Club Advisor Department of Chemistry & Biochemistry|University of Michigan-Flint

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