Itaconic acid → Methylsuccinic acid

HRID 1638416

반응식

HRID 1638416 반응식
CO.[C:3]([OH:11])(=[O:10])[C:4]([CH2:6][C:7]([OH:9])=[O:8])=[CH2:5].C(N(CC)CC)C.Cl([O-])(=O)(=O)=O>[H][H].C1CCCCC=CC=1.[Rh]>[CH3:5][CH:4]([CH2:6][C:7]([OH:9])=[O:8])[C:3]([OH:11])=[O:10]

참가 물질

7

반응물 4

HCID 811Itaconic acidHCID 887MethanolHCID 8471TriethylamineHCID 123351Perchlorate

생성물 1

HCID 10349Methylsuccinic acid수율 91.9%

시약·촉매·용매 2

HCID 86743496Rhodium cyclooctadiene촉매HCID 178418361HCID 178418361, 화합물용매

실험 절차

To 10 ml of methanol were added 1.301 g (10 m-mol) of itaconic acid, 1.4 ml (10 m-mol) of triethylamine and 8.8 mg (0.01 m-mol) of rhodium cyclooctadiene BCPM complex perchlorate ([Rh(COD)BCPM]+ClO4-). The mixture was stirred in hydrogen atmosphere at 1 atm. for 20 hours at 20° C. and the reaction mixture was concentrated under reduced pressure. To the residue was added 20 ml of an aqueous solution of 1N-NaOH and the mixture was filtered to remove insoluble matter. The filtrate was made acidic with 6N-HCl and extracted with ether. From the ethereal extract, 2-methylsuccinic acid was obtained quantitatively by distilling off the solvent. It was confirmed that the itaconic acid had been converted by 100% in view of a result of 1H-NMR. [α]D22 =-15.51° (c=2.00, EtOH)(optical yield: 91.9%).

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added 20 ml of an aqueous solution of 1N-NaOH
  3. filtrationthe mixture was filtered
  4. customto remove insoluble matter
  5. extractionextracted with ether
  6. extractionFrom the ethereal extract

출처 및 근거

ORD 기록
ord-7d03ffc5cc244da6af6d63be9e93b916
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04879389

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