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

HRID 258333
ノート
印刷プレビュー

反応式

HRID 258333 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran
溶媒

実験手順

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##

後処理

  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

出典と根拠

ORDレコード
ord-ee8cc258438149858b87c1354f220b57
出典データセット
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05266661

反応ノート

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