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

HRID 326801
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HRID 326801 반응식
[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
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참가 물질

6

반응물 3

HCID 785Hydroquinone2회HCID 7488Terephthaloyl chloride2회HCID 14798Sodium Hydroxide2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028
Tetrahydrofuran
용매

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-1308d32fa90d4c0786e452b0a24b96ed
출처 데이터셋
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05270406

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