Sulfuric Acid → 3-(Trimethylsilyl)propionic acid

Participants

Reaction Conditions

Reaction Steps

To 12.5 mL of water was added 8.73 g (0.0873 mole) of chromium trioxide which was mixed until all solid had dissolved. This solution was immersed in an ice/water bath, and 13.4 g (7.3 mL, 0.137 mole) of concentrated sulfuric acid (18M) was added cautiously. This was followed by the addition of 25 mL of water. The solution was then cooled to 0°-5° C. and added to a stirred solution of 16.5 g (0.125 mole) of 4,4-dimethyl-4-silapentanol in 800 mL of acetone which had been cooled to 0°-10° C. in an ice/water bath. During the addition the temperature was maintained at 20° C., and stirring was continued for three hours after the addition was complete. At the conclusion of this period sodium bisulfite was added to the reaction mixture in small portions until the brown color of chromic acid had disappeared from the upper layer. The two layers were separated, and the dense, green lower layer was extracted with 200 mL of petroleum ether. The layers were separated, and the upper layer was added to the upper layer which had been previously separated. This caused two phases to form. The layers were separated, and the lower layer was added to the lower layer from the reaction mixture. The combined lower layers were extracted three times with 200 mL of petroleum ether. The extracts were combined with the previously separated petroleum ether extract, and this mixture was successively washed twice with a saturated aqueous solution of sodium chloride, twice with a saturated aqueous solution of sodium bicarbonate, and finally with a saturated aqueous solution of sodium chloride. After being dried over anhydrous magnesium sulfate, the solvent was evaporated from the combined extracts under reduced pressure, leaving 4,4-dimethyl-4-silapentanoic acid as a residue. The NMR spectrum was consistent with the proposed structure. This is the method described in Organic Synthesis, Vol. V, p 866.

Provenance & Evidence