Synthetic Route of 558-42-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, molecular weight is 108.5667, as common compound, the synthetic route is as follows.
[00351j Step 1: methyl 3-chloro-4-(2-hydroxy-2-methylpropoxy)benzoate [00352j A 500 ml 3 neck RB flask was fitted with a mechanical stirrer,a J-Kem temperature probe/controller, an addition funnel, a water cooled reflux condenser and a nitrogen inlet/outlet. The vessel was charged under a nitrogen atmosphere with methyl 3-chloro-4-hydroxy-benzoate (10 g, 53.6 mmol) and methylalcohol (40 ml) which provided a clear pale yellow solution. Stirring was commenced and the pot temperature was recorded at 19 °C. The vessel was then charged with potassium carbonate (30 g, 0.21 mol) added as a solid in one portion which resulted in an exotherm to 23 °C. Note: The potassium carbonate was ground to a fine powder prior to use. The resulting suspension was continued to stir at rt for 15 mm and thentreated with 1-chloro-2-methyl-propan-2-ol (11.6 g, 0.11 mol) added neat dropwise via addition funnel over 10 mm. The resulting reaction mixture/suspension was then heated to 70 °C and stirred for 20 h. The reaction mixture was cooled to rt and diluted with ethyl acetate (250 ml). The mixture was filtered through a glass fit Buchner funnel with a 10 mm layer of Celite. The filter cake was washed with ethyl acetate (2 x100 ml). The filtrate was transferred to a separatory funnel and partitioned with 1 M aqueous NaOH (250 ml). The organic was removed and washed with 1 M aqueous NaOH (2 x 150 ml), saturated aqueous sodium chloride (150 ml), dried over sodium sulfate (250 g) and filtered through a glass frit Buchner funnel. The filtrate was concentrated under reduced pressure to provide methyl 3-chloro-4-(2-hydroxy-2-methylpropoxy)benzoate (9.0 g, 65percent) as a clear pale yellow oil. The material was used without further purification in the next synthetic step. ESI-MS mlz caic. 258.7, found 259.2 (M+1) Retention time: 1.46 mm (3 mm run).
The chemical industry reduces the impact on the environment during synthesis 558-42-9, I believe this compound will play a more active role in future production and life.
Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DENINNO, Michael, Paul; ANDERSON, Corey; CONROY, Erica, Lynn; FRIEMAN, Bryan, A.; GROOTHENHUIS, Peter, Diederik Jan; HADIDA-RUAH, Sara, Sabina; HURLEY, Dennis, James; PIERRE, Fabrice Jean, Denis; SILINA, Alina; UY, Johnny; ZHOU, Jinglan; WO2015/6280; (2015); A1;,
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