August 14, 2020, 10:10:53 PM
Forum Rules: Read This Before Posting


Topic: alkaline hydrolysis of a methyl ester  (Read 853 times)

0 Members and 1 Guest are viewing this topic.

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 1050
  • Mole Snacks: +69/-5
Re: alkaline hydrolysis of a methyl ester
« Reply #15 on: July 11, 2020, 05:55:55 AM »
If t-BuOK gives hydrolysis I think it can be old reagent containing KOH?

Offline wildfyr

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 1517
  • Mole Snacks: +161/-9
Re: alkaline hydrolysis of a methyl ester
« Reply #16 on: July 13, 2020, 09:14:44 AM »
Buying potassium tert butoxide fresh is very recommended. It is very hygroscopic, and unless stored in a glove box it will almost certainly contain at least trace tert butanol and KOH.

Its also possible another reagent in your reaction had some water, which formed KOH in situ.

Offline kriggy

  • Chemist
  • Sr. Member
  • *
  • Posts: 1410
  • Mole Snacks: +119/-15
Re: alkaline hydrolysis of a methyl ester
« Reply #17 on: July 23, 2020, 07:11:29 AM »
Buying potassium tert butoxide fresh is very recommended. It is very hygroscopic, and unless stored in a glove box it will almost certainly contain at least trace tert butanol and KOH.

Its also possible another reagent in your reaction had some water, which formed KOH in situ.

If t-BuOK gives hydrolysis I think it can be old reagent containing KOH?

Ah right, didnt realize that at the time. I wanted to do transesterification but thought tBuOK is too bad nucleophile for that.

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 1050
  • Mole Snacks: +69/-5
Re: alkaline hydrolysis of a methyl ester
« Reply #18 on: July 23, 2020, 08:29:04 AM »
If you have good NaH you can make t-BuONa, that reagent is similar as t-BuOK, ust mix t-BuOH and NaH and evaporate. You can also use Na-metal and t-BuOH.
« Last Edit: July 23, 2020, 10:15:33 AM by rolnor »

Sponsored Links