Itaconic acid → Methylsuccinic acid

HRID 1741810

반응식

HRID 1741810 반응식
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].C(O)(C)C>O1CCCC1>[CH3:3][CH:2]([CH2:4][C:5]([OH:7])=[O:6])[C:1]([OH:9])=[O:8]

참가 물질

4

반응물 2

HCID 811Itaconic acidHCID 3776Isopropanol

생성물 1

HCID 10349Methylsuccinic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

In a 20 ml-volume Schlenk's tube were charged 65.0 mg (0.5 mmole) of itaconic acid and 14.91 mg (0.01 mmole) of [RuH((-)-BINAP)2 ]PF6, and 2.5 ml of tetrahydrofuran (THF) and 2.5 ml (32.7 mmole) of isopropyl alcohol were added thereto. The mixture was heated at reflux in an oil bath at 85° C. for 24 hours. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 20 ml of a 1M sodium hydroxide aqueous solution and washed three times with each 10 ml portions of chloroform. The aqueous layer was adjusted to a pH of 1 with concentrated hydrochloric acid and then extracted three times with each 10 ml portions of diethyl ether. The combined ether layer was dried over magnesium sulfate, and the solvent was removed to give 47 to 60 mg of methylsuccinic acid as a white solid.

후처리

  1. additionwere added
  2. temperatureThe mixture was heated
  3. customThe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in 20 ml of a 1M sodium hydroxide aqueous solution
  5. washwashed three times with each 10 ml portions of chloroform
  6. extractionextracted three times with each 10 ml portions of diethyl ether
  7. dry with materialThe combined ether layer was dried over magnesium sulfate
  8. customthe solvent was removed

출처 및 근거

ORD 기록
ord-2f120d45741c4147aafff66717a49808
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334758

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