Hexacoralli
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Registered: 14-1-2025
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synthesis of t-butyl thiol !
A month ago, I published a post describing an idea of attempting t butyl thiol synthesis. I was discouraged from that because of its allegide horrible
smell, but...I finally decided to did it.
1. t butyl alcohole was left to react with hydrochloric acid for about 10 minutes, and that way obtained tert butyl chloride was separated with a
separation funnel and then dried with anhydrous calcium chloride.
2. 5 grams of this alcohole chloride were stirred and slightly heated (after 1,5 h of reaction) with equimolar amount of magnesium shaves in around 30
ml of diethyl ether for about 2-3 hours. Iodine was used as catalyst. (grignard reaction) The magnesium didn't fully react, but wasn't separated from
the mixture. The flask was left outside for 2 days covered with aluminium foil. Temperature outside was 0 Celsius degrees. After 2 days, mixture was
filled with ether upto 50 ml.
3.This way obtained tert butyl magnesium chloride solution in diethyl ether was let to react with toluene solution of 0,2 grams of elemental sulfur.
Toluene was added in amount that let the sulfur fully diussolve. About 7 ml of grignard reagent in ether was used, but the reagents amounts weren't
stoichiometric. The reaction was let to react 20 minutes with slight heating. Then ~25% solution of NaOH was used to extract probably formed t butyl
thiol in its alkaline form. Great amount of sulfur percipitated out of the solution so I thought that reaction probably wasn't completed lucky and
left the water layer for about 2 weeks.
4. Smell testing
To get out the thiol out of the solution, I acidified the flask containing the thiol with large excess of muriatic acid. For the first moment only
slight smell resembling that from muriatic acid was smelled, but after a couple of minutes relatively strong gas/garlic/phosphine resembling odour was
emited from the flask much more intense that the pure muriatic acid itself. If the reaction yield was 100% the thiol concentration in solution would
reach 1% but it definitely wasn't.
[Edited on 12-2-2025 by Hexacoralli]
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Hexacoralli
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Posts: 5
Registered: 14-1-2025
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I have a photo of reaction with sulfur , but have problem with sending 
[Edited on 12-2-2025 by Hexacoralli]
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