Hydrochloric Acid → 2,2-Bis(4-nitrobenzyl)-1,3-propandiol

Participants

Reaction Steps

About 2 mole of 1-bromomethyl)-4-nitrobenze and about 1 mole of dimethyl malonate were mixed with excess methyl ethyl ketone (MEK) which was mixed with potassium carbonate at a temperature of about 50° C. for about 3 hours. After adding excess water at temperature of about 25° C., the above materials were precipitated to obtain about 1 mole of dimethyl 2,2-bis(4-nitrobenzyl)malonate. About 1 mole of dimethyl 2,2-bis(4-nitrobenzyl)malonate was mixed with water and tetrahydrofurane (THF) which was mixed with lithium hydroxide, and dimethyl 2,2-bis(4-nitrobenzyl)malonate at a temperature of about 25° C. for about 22 hours. After adding about 1 N of hydrochloric acid at a temperature of about 25° C., excess water and ether were added to extract about 1 mole of 2,2-bis(4-nitrobenzyl)maloic acid. THF and borane were added to about 1 mole of 2,2-bis(4-nitrobenzyl)maloic acid and THF, borane at a temperature of about 25° C. for about 20 hours. After adding excess water and ethyl acetate, about 1 mole of 2,2-bis(4-nitrobenzyl)propane-1,3-diol was obtained. Formaldehyde was added to about 1 mole of 2,2-bis(4-nitrobenzyl)propane-1,3-diol, and 2,2-bis(4-nitrobenzyl)propane-1,3-diol at a temperature of about 80° C. for about 30 minutes. Hydrogen bromide was added to, and 2,2-bis(4-nitrobenzyl)propane-1,3-diol, formaldehyde, and hydrogen bromide were reacted at a temperature of about 25° C. for about 3 hours to obtain about 1 mole of 2,2-bis((bromomethoxy)methyl)-1,3-bis(4-nitrophenyl)propane. After adding triphenylphosphine and carbon dichloride to 2,2-bis((bromomethoxy)methyl)-1,3-bis(4-nitrophenyl)propane at a temperature of about 23° C. for about 2 hours, about 1 mole of 4-formylphenyl 4-(4,4,4-trifluorobutoxy)benzoate was mixed with excess sodium hydride and THF at a temperature of about 23° C. for about 18 hours. Then, zinc chloride and carbon dichloride are added at a temperature of about 40° C. for about 16 hours to obtain about 1 mole of the compound represented by Chemical Formula 6.

Provenance & Evidence