Application of 3-chloro-2,2-dimethyl-1-propanol_Industrial additives

Background and overview^[1]

3-Chloro-2,2-dimethyl-1-propanol can be used as a pharmaceutical and chemical synthesis intermediate. If 3-chloro-2,2-dimethyl-1-propanol is inhaled, move the patient to fresh air; if skin contact occurs, remove contaminated clothing and wash skin thoroughly with soap and water, if necessary If you feel unwell, seek medical attention; if eye contact occurs, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.

Apply^[1]

3-Chloro-2,2-dimethyl-1-propanol can be used as an intermediate for pharmaceutical and chemical synthesis. For example, the following reactions can occur:

The specific steps are:

Step 1: Add 71.8g (0.586mol) of 3-chloro-2,2-dimethyl-1-propanol into DMSO (210mL) containing 86g of NaI (0.574mol) and 75g of sodium azide (1.15mol) ) mixture and added to the flask, flushed with nitrogen, the mixture was stirred vigorously on a 140°C bath under a reflux condenser for 38 hours, the reaction mixture was cooled to 90°C and diluted with water to a total volume of 900mL, washed with diethyl ether (2× The mixture was extracted with water (0.5 L), the organic extracts were washed with water (0.5 L), combined, dried (magnesium sulfate) and evaporated. The residue was fractionated at 0.1 Torr, and the pure product was distilled at 30-35°C/0.1 Torr to obtain a colorless slightly viscous liquid (80.5%). 1H (CDCl3, MHz): 3.380 (d, 5.1Hz, 2H), 3.219 (s, 2H), 1.853 (t, 5.2Hz, 1H), 0.916 (s, 6H)

Step 2: 28.6g of naphthalene (223mmol, purified by crystallization from MeOH followed by sublimation) and 7.35g of freshly cut metal (188mmol, cut into ~0.3×0.3×2cm pieces under mineral oil and purified with heptane Rinse briefly) and mix below. In a modified Schlenk storage flask equipped with a glass-coated stir bar, connect the purged THF solvent line, evacuate the flask to below 0.03 Torr and backfill with dry Ar, then introduce anhydrous purified THF (0.45L) In the flask, close the flask stopcock and stir the mixture overnight (16 hours), then let it sit for 20 minutes. The resulting dark green solution was used on the same day, transferred as needed via cannula under slight positive pressure of Ar (carefully withdrawn from the top to avoid disturbing precipitated impurities at the bottom of the flask).

Main reference materials

[1] US20130178600. POLY(ETHYLENE GLYCOL) DERIVATIVES FOR CLICK CHEMISTRY