477727-71-2

Upstream product

• 110-86-1 pyridine 
• 119015-52-0 1-(1,2-dichloroethyl)-4-methoxybenzene 
• 857590-90-0 1-(1-ethoxy-2-chloro-ethyl)-4-methoxy-benzene 
• 563-79-1 2,3-Dimethyl-2-butene 
• 91309-65-8 3-chloro-3-(p-methoxybenzyl)diazirine 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 623-91-6 diethyl Fumarate 
• 768-60-5 4-methoxyphenylacetylen 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 637-69-4 4-Methoxystyrene 
• 623-46-1 1,2-dichloro-2-ethoxyethane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Downstream Products

• 1515-95-3 p-ethylanisole 
• 123-11-5 4-methoxy-benzaldehyde 
• 79958-53-5 (E)-1-(3,3-dimethylbut-1-en-1-yl)-4-methoxybenzene 
• 136431-36-2 3,6-Bis-dimethylamino-9-(4-methoxy-phenylethynyl)-9H-fluoren-9-ol 

Relevant academic research and scientific papers

Transition metal free large-scale synthesis of aromatic vinyl chlorides from aromatic vinyl carboxylic acids using bleach

While continuing our research on Hunsdiecker reaction, we came across an interesting application of bleach, sodium hypochlorite (NaOCl) for decarboxylative chlorination reaction. The reaction is easily scaled up to 10 mmol. The reaction has good tolerance towards wide variety of functional groups. The reaction has mild conditions and gave relatively high chemical yield of the desired product.

Olefin cross-metathesis with vinyl halides

The first successful example of olefin cross-metathesis with chloroalkenes is reported. The Royal Society of Chemistry.

Cu(II)-promoted oxidative homocoupling reaction of terminal alkynes in supercritical carbon dioxide

Oxidative homocoupling reaction of various terminal alkynes in supercritical carbon dioxide (scCO2) has been reported. The final optimized reaction conditions for the reaction in ScCO2 were determined to be cupric chloride (2 mmol), sodium acetate (2 mmol), methanol (1 mL) and CO2 (14 MPa) at 40 °C. Sodium acetate was superior to pyridine in the present reaction system. Methanol, as a co-solvent of ScCO 2, was necessary to help dissolve the inorganic salt and facilitated the reaction. Higher solubility of cupric chloride in the scCO 2-methanol medium than other cupric salts, e.g. CuSO4, Cu(NO3)2, Cu(OAc)2 and cupric bromide, guaranteed its high catalytic ability. Variations of the pressure of ScCO 2 and temperature in a certain range have almost little impact on the reaction efficiency. A mechanism involving copper(II)-acetylide complex was supposed in which AcO- or Cl- instead of N-containing compounds acted as ligands. The reaction system in ScCO2 is an effective and environmental-friendly alternative to the previous methods of homocoupling of terminal alkynes involving volatile organic compounds. Georg Thieme Verlag Stuttgart.

Carbanions phosphonate prepares par voie electrochimique: formation et reactivite vis-a-vis d'un aldehyde

Reactivity towards p-methoxybenzaldehyde (ArCHO) of electrochemically generated phosphonate carbanions has been investigated.Electrolyses were carried out at a mercury cathode in DMF and two routes to the desired carbanion have been compared: (i) Deprotonation of phosphonates of general formula (EtO)2P(O)CHYW (Y = W = Cl; Y = H, W = Cl; Y = Cl, W = CO2Et; Y = H, W = CO2Et; Y = CH3, W = CO2Et; Y = Cl, W = CH3), by the bases resulting from the electroreduction of azobenzene; addition of the carbanion formed onto the carbonyl group takes place and leads to the adduct (EtO)2P(O)CYW(Ar)O-. (ii) Two-electron reduction of halophosphonates (EtO)2P(O)CXYW (X = Cl, Y and W as above; X = Br, W = CO2Et, Y = Cl, Br, or CH3); when no H atom is present on the carbon bearing the phosphonate group (Y and W no = H), the same evolution leading to the above adduct is observed, on the contrary, when Y = H, the electrogenerated carbanion deprotonates the substrate and the resulting carbanion (EtO)2P(O)CXW reacts with the aldehyde; giving the adduct (EtO)2P(O)CXW(Ar)O-.Evolution of the intermediate adduct depends on the substituents Y (or X) and W: when W = CO2Et, whatever the nature of Y (or X), diethyl phosphate is eliminated with formation of the ethylenic ArCH=CWY (or X) (Wittig-Horner reaction); the same evolution is observed when Y = W = Cl.When W = Cl and Y = H or CH3, the final product is the phosphonate epoxyde resulting from chloride elimination (Darzens reaction).Chemo- and stereoselectivity depend only on the nature of Y and W but are independent of the mode of generation of the carbanion.Yields are limited by side-protonation reactions, which are related to the basicity of the phosphonate carbanions.Analysis of the results permits selection of the optimal electrolysis conditions for purposes of synthesis.Key words: electrosynthesis, electrogenerated bases, phosphonates, Wittig-Horner.

Thermolysis and Photolysis of 3-Chloro-3-benzyldiazirines in Alkenes: Evidence for a Carbene-Alkene Complex

Photolysis and thermolysis of substituted 3-chloro-3-benzyldiazirines in alkenes yielded cyclopropanes and chlorostyrenes as products.The results suggest that the cyclopropanation of benzylchlorocarbenes is independent of substituents.However, 1,2-hydrogen migration is accelerated by OCH3 or CH3 substituents, and is decelerated by a Cl substituent on the phenyl ring.These results support the existence of an energy barrier to 1,2-H migration.Evidence is provided for carbene-alkene complexation.