4-Hydroxybenzoic Acid → HCID 21803579, compound

Participants

Reaction Steps

Separately, 60 g of 4-hydroxybenzoic acid was dissolved in 500 ml of ethanol, and a solution of 15 g of NaOH in 500 ml of water was added thereto. To the mixture was added 50 g of benzyl chloride, followed by stirring for 2 hours at room temperature and 2 hours of heat refluxing. After distilling off the solvent, the product was recrystallized from ethanol to obtain 40 g of benzyl-4-hydroxybenzoic acid. Then, 17 g of the benzyl-4-hydroxybenzoic acid was dissolved in 100 ml of pyridine, and 8 g of terephthaloyl chloride was added thereto, followed by stirring for 2 hours at room temperature and for 1 hour at 70° C. The reaction mixture was added to 500 ml of 2M-HCl to obtain 10 g of bis(4-benzyloxycarbonylphenyl)terephthalate, which was then added to 150 ml of trifluoroacetic acid, followed by addition of 10 ml of 33% HBr solution in acetic acid and reaction for 12 hours at room temperature. Acetone was added to the reaction mixture to result in a precipitate, which was then separated and washed with acetone to obtain 4 g of bis (4-carboxyphenyl)terephthalate. Then, 2 g of the diacid was mixed with 40 ml of SOCl2, followed by 2 hours of heat refluxing, reduced pressure distillation for removal of an excess of SOCl2, addition of 1,2-dichloroethane and addition of a solution of 1 g of the compound of the formula (IX) in 5 ml of pyridine. The mixture was subjected to reaction at 60° C. for 3 hours and at room temperature for 10 hours. The reaction product was re-precipitated from acetone and washed with water to obtain a polymer mesomorphic compound of the following formula (X) (ηinh =0.02 dl/g): ##STR38##

Provenance & Evidence