Hydroquinone → Bis(4-hydroxyphenyl) benzene-1,4-dicarboxylate

HRID 258333Notes

Reaction equation

HRID 258333 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](Cl)(=[O:19])[C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.[OH-:21].[Na+]>O1CCCC1.O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][C:9](=[O:19])[C:10]2[CH:18]=[CH:17][C:13]([C:14]([O:21][C:5]3[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][CH:4]=3)=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 785Hydroquinone2×HCID 7488Terephthaloyl chloride2×HCID 14798Sodium Hydroxide

Product 1

HCID 20317210Bis(4-hydroxyphenyl) benzene-1,4-dicarboxylateYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

bis(4-Hydroxyphenyl)terephthalate (Structure IV) is synthesized by the reaction of hydroquinone with terephthaloyl chloride through the addition of NAOH. The hydroquinone (162.7 grams, 1.48 moles) and terephthaloyl chloride (150.0 grams, 0.74 moles) are first dissolved in 750 ml of tetrahydrofuran in a two liter round bottom flask which is stirred. The NaOH (59.1 grams, 1.48 moles) in 300 ml of deionized water is next added dropwise using an addition funnel over a one hour period and the mixture is then allowed to stir an additional two hours at ambient temperature (pH=6). The precipitate obtained is collected by vacuum filtration and then added to 500 ml of deionized water and 1000 ml of methanol. This solution is stirred for one hour at 40°-55° C. and then filtered. The solids collected here are added to 1100 ml of anhydrous methanol and stirred at 40°-55° C. for one hour followed by a third filtration. The resultant solids are then dried in a 80° C. vacuum oven. This final product (111.9 grams, yield=43.3%) exhibited a sharp melting endotherm by DSC at 415° C. ##STR12##

Workup

  1. customover a one hour
  2. stirringto stir an additional two hours at ambient temperature (pH=6)
  3. customThe precipitate obtained
  4. filtrationis collected by vacuum filtration
  5. additionadded to 500 ml of deionized water and 1000 ml of methanol
  6. stirringThis solution is stirred for one hour at 40°-55° C.
  7. filtrationfiltered
  8. customThe solids collected here
  9. additionare added to 1100 ml of anhydrous methanol
  10. stirringstirred at 40°-55° C. for one hour
  11. filtrationfollowed by a third filtration
  12. customThe resultant solids are then dried in a 80° C. vacuum oven

Sources & evidence

ORD record
ord-ee8cc258438149858b87c1354f220b57
Source dataset
uspto-grants-1993_11
Patent number
US05266661

Reaction notes

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