December 03, 2021, 02:21:00 PM
Forum Rules: Read This Before Posting


Topic: Plausible Starting Materials?  (Read 5315 times)

0 Members and 1 Guest are viewing this topic.

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Plausible Starting Materials?
« Reply #15 on: April 22, 2013, 10:58:34 PM »
I find two things troubling. Is 4-hydroxycyclohexanone in the Aldrich catalog? Cyclohexanone undergoes an aldol condensation with hydroxide or alkoxides.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline azncuzin202

  • Regular Member
  • ***
  • Posts: 29
  • Mole Snacks: +0/-0
Re: Plausible Starting Materials?
« Reply #16 on: April 23, 2013, 12:24:17 AM »
Yeah,  4-hydroxycyclohexanone is in the catalogue. http://www.sigmaaldrich.com/catalog/product/aldrich/t292184?lang=en&region=US

Offline TwistedConf

  • Regular Member
  • ***
  • Posts: 67
  • Mole Snacks: +10/-2
Re: Plausible Starting Materials?
« Reply #17 on: April 23, 2013, 12:34:28 PM »
Cyclohexanone undergoes an aldol condensation with hydroxide or alkoxides.

It probably depends on how sophisticated the instructor is. Side reaction is certainly a concern for maximum yield. Could you make the case for adding 1eq of NaH in a sea of CH3I? Perhaps. Alpha-methylating the ketone might creep in.

Otherwise- he needs to think about protecting group strategy. Mask the carbonyl before alkylating. Certainly makes the assignment more interesting- and shows more sophistication.

By the way--- this is a known compound with actual preps in the literature.

Offline azncuzin202

  • Regular Member
  • ***
  • Posts: 29
  • Mole Snacks: +0/-0
Re: Plausible Starting Materials?
« Reply #18 on: April 25, 2013, 02:17:44 PM »
Would alpha methylation be guaranteed or would it only give a minor product?

Sponsored Links