Reference of 3236-48-4 ,Some common heterocyclic compound, 3236-48-4, molecular formula is C8H16O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Synthesis ofDIPP-CDM : Anhydrous Na2C03 (8.54 g) was dried in a 250 mL flask for 1.5 h at 180 °C under vacuum. The flask was cooled and flushed with N2. Then, CDM (5.76 g, 40 mmol) and [Ir(cod)Cl]2 (0.97 g) were added. The mixture was dried using several nitrogen- vacuum purging cycles. Then, 24 mL IPPA and 40 mL toluene were added. The mixture was heated at 100 °C. Six hours later, the mixture was cooled and diluted with ether, filtered, and dried under vacuum. The residue was extracted with hexane. Hexane was removed by rotary evaporation. DIPP-CDM (2.7 g) was (0423) recrystallized from ACN twice and dried under vacuum. (0424) The synthesis was confirmed by high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR). It is notable that the acid sensitivity of DIPP-CDM prevents its detection when trifluoro acetic acid, a common HPLC additive, was present in the eluent. Signals of DIPP-CDM were also not observed when CDC13 was used as an NMR solvent, since CDC13 can react with light and oxygen to form phosgene and DC1. It is notable that DIPP was so acid sensitive that DIPP hydrolyzed completely in the silica column even in the presence of triethylamine. In addition, the polarity of DIPP and the transacetate side product during the reaction (such as mono- ester and di-ester substituted compounds) are so similar that they come off of a basic aluminum oxide column together rapidly, leading to the failure of purification. (0425) DIPP-CDM was also purified by column chromatography (CombiFlash® Rf, 100 g HP CI 8, Teledyne Isco, Lincoln, NE, USA). To prevent the hydrolysis of monomer in H20/ACN, 0.1percent TEA was added. C18 column chromatography yielded a higher quantity of polymerization grade monomer (6.8g, 75 wtpercent) than did recrystallization (30 wtpercent). The chemical shifts in the NMR spectra of DIPP-CDM were assigned as below (C6D6 as NMR solvent, Cambridge Isotope Laboratories, Inc., Tewksbury, MA, USA): 1H NMR (C6D6, ppm, 400 MHz): delta 3.93-3.88 (d, = 9.0 Hz, 4H), 3.38-3.35 (d, = 6.65 Hz, 4H), 1.81 (s, 6H), 1.79-1.73 (d, = 6.65 Hz, 4H), 1.61-1.47 (m, 2H), 0.93-0.81 (m, 4H) 13C NMR (C6D6, ppm, 400 MHz): delta 159.88, 80.93, 72.48, 37.51, 29.18, 20.77.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 3236-48-4, trans-1,4-Cyclohexanedimethanol, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; CHILDREN’S MEDICAL CENTER CORPORATION; KOHANE, Daniel, S.; GUO, Shutao; (110 pag.)WO2017/189953; (2017); A1;,
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