4-Hydroxybenzoic Acid → HCID 21803579, compound

HRID 1769921Notes

Reaction equation

HRID 1769921 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C.O>[CH2:13]([C:9]1[CH:10]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=1[C:6]([OH:8])=[O:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 21803579HCID 21803579, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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##

Workup

  1. temperatureof heat
  2. temperaturerefluxing
  3. distillationAfter distilling off the solvent
  4. customthe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-15237b9ab2cc48ee9e8ea39616d8d716
Source dataset
uspto-grants-1995_01
Patent number
US05384069

Reaction notes

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