Dicyclopentadiene → 4,5,6,7-Tetrahydro-4,7-methanoisobenzofuran-1,3-dione

HRID 1253357

반응식

HRID 1253357 반응식
C1CC=CC=1.C1[CH:10]2[CH:11]3[CH:15]=[CH:14][CH:13]([CH:9]2C=C1)[CH2:12]3.[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH:18]=[CH:17]1.[CH:23]12[CH2:29][CH:26]([CH:27]=[CH:28]1)[CH:25]([C:30]([OH:32])=O)[CH:24]2[C:33]([OH:35])=[O:34].B(F)(F)F.CCOCC>>[C:11]12([C:17]3=[CH:18][C:19]([O:21][C:16]3=[O:22])=[O:20])[CH2:12][CH:13]([CH2:9][CH2:10]1)[CH:14]=[CH:15]2.[CH:26]12[CH2:29][CH:23]([CH2:28][CH2:27]1)[C:24]1[C:33]([O:35][C:30](=[O:32])[C:25]2=1)=[O:34]

참가 물질

7

반응물 5

HCID 6492DicyclopentadieneHCID 7612Cyclopentadiene3회HCID 7923Maleic Anhydride2회HCID 8000Boron trifluoride etherateHCID 979655-Norbornene-2,3-dicarboxylic acid

생성물 2

HCID 122074964,5,6,7-Tetrahydro-4,7-methanoisobenzofuran-1,3-dioneHCID 86587753Norbornene-maleic anhydride

반응 조건

온도
100 °C

실험 절차

Mixed polybasic anhydride containing a plurality of 1,2 anhydrides is obtained by distilling, at 200° C., 66.10 gms. (1 mole) of cyclopentadiene directly from dicyclopentadiene into a reactor containing 98.06 gms. (1 mole) of maleic anhydride, heated to a temperature of 55° C. When the transfer is complete, the reaction mixture is heated to 100° C. for 2 hours. The reaction mixture is then stripped of any excess cyclopentadiene at 120° C. at 1 atmosphere. The resulting Diels-Adler adduct of cyclopentadiene and maleic anhydride is the anhydride of cis.-5-norbornene-2,3-dicarboxylic acid. The reaction mixture is cooled to 50° C., and 4.90 gms. (0.03 moles) of boron trifluoride etherate is added slowly with stirring. The reaction mixture exotherms to 65° C. after which it is heated to 125° C., to decompose the BF3OEt and then cooled. The reaction is quenched by mixing with 3 liters of 10% sodium bicarbonate. The mixture is then neutralized with dilute 5% hydrochloric acid. The mixed polybasic anhydride of norbornene-2,3-dicarboxylic acid anhydride is obtained as a fine tan power, Mp. 200° C., and used for foam preparation without further purification.

후처리

  1. customis obtained
  2. distillationby distilling, at 200° C.
  3. temperatureThe reaction mixture is cooled to 50° C.
  4. customexotherms to 65° C.
  5. temperatureis heated to 125° C.
  6. temperaturecooled
  7. customThe reaction is quenched
  8. additionby mixing with 3 liters of 10% sodium bicarbonate
  9. additionwith dilute 5% hydrochloric acid

출처 및 근거

ORD 기록
ord-28376501b3024e99810eecece371ebb7
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04748255

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