2-PROPANOLE-D7 synthesis

Yield:19214-96-1 61%

Reaction Conditions:

with water-d2;sodium chloride

Steps:

(CD₃)₂CHOD:

General procedure: The glassware used in this procedure went through the three cycles of flame drying and rinsing with D₂O to remove protons from the glass surface. NaCl (1.57 g) was dissolved in 4.7 ml of D₂O, forming 25 wt% solution. The solution was divided into two equal portions via syringe. First portion was combined with 2 mL of (CD₃)₂CHOH and was shaken well for a few seconds (Ratio of D₂O to IPA is 5:1). After that, two layers were formed with the top layer being IPA and the botom one being brine. IPA layer was collected and poured over second portion of the brine, so the salting out could be conducted again. The solution was shaken and the top layer was separated and placed into the dry 20 mL flask with the stir bar. CaH₂ was added to the flask in a small portions to remove remaining D₂O and the flask was constantly cooled in liquid nitrogen to avoid any overheating inside. CaH₂ was added to the flask until the visible formation of the gas has stopped. After that, (CD₃)₂CHOD was distilled under vacuum, dried over CaH₂ overnight and vapor transferred to the flask at which it was stored (1.22 mL, 61%). The degree of deuteration of the hydroxyl group reached >95%.

References:

Cherepakhin, Valeriy;Demianets, Ivan;Lauridsen, Paul J.;Maertens, Alexander;Mallikarjun Sharada, Shaama;Williams, Travis J. [Polyhedron,2020,vol. 182] Location in patent:supporting information