Diethyl allylmalonate → 2-Allyl-3-methylsuccinic acid

HRID 1074592노트

반응식

HRID 1074592 반응식
C([O:3][C:4](=[O:14])[CH:5]([CH2:11][CH:12]=[CH2:13])C(OCC)=O)C.C([O:17][C:18](=[O:22])[CH:19](Br)[CH3:20])C>COCCOCCOC>[CH2:11]([CH:5]([CH:19]([CH3:20])[C:18]([OH:17])=[O:22])[C:4]([OH:14])=[O:3])[CH:12]=[CH2:13]

참가 물질

4

반응물 2

HCID 74900Diethyl allylmalonateHCID 79040Ethyl 2-bromopropionate

생성물 1

HCID 199806952-Allyl-3-methylsuccinic acid수율 96%

시약·촉매·용매 1

HCID 8150Diglyme용매

실험 절차

90.5 g (0.5 moles) of 2-allylmalonic acid diethyl ester are reacted in diethylene glycol dimethyl ether with 0.5 moles of alcohol-free sodium ethoxide. 0.5 moles of 2-bromopropionic acid ethyl ester is added dropwise to this solution, with stirring. The mixture is heated for a further 2 hours under reflux and the solvent is then removed. The residue is subsequently subjected to hydrolysis in alcoholic KOH. After drying the organic layer that has separated, it is fractionated. The desired 2-allyl-1-methylethane-tricarboxylic acid 1,2,2-triethyl ester boils under 0.02 torr at 92° to 95° C. The ester is hydrolyzed in alcoholic KOH and, after working up in the customary manner, is decarboxylated at 170° C. with water being split off. The anhydride of 2-allyl-3-methylsuccinic acid (b.p. at 0.1 torr: 108° to 110° C.) is obtained in a 96% yield (based on the ester).

후처리

  1. temperatureThe mixture is heated for a further 2 hours
  2. temperatureunder reflux
  3. customthe solvent is then removed
  4. customThe residue is subsequently subjected to hydrolysis in alcoholic KOH
  5. customAfter drying the organic layer that
  6. customhas separated
  7. customboils under 0.02 torr at 92° to 95° C
  8. customis decarboxylated at 170° C. with water being
  9. customsplit off

출처 및 근거

ORD 기록
ord-2e09f620998b4121b9648bda659f5ebe
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04393220

반응 노트

불러오는 중…