Diethyl allylmalonate → 2-Allyl-3-methylsuccinic acid

HRID 1074592ノート

反応式

HRID 1074592 の反応式
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]

参加物

4

反応物 2

HCID 74900Diethyl allylmalonateHCID 79040Ethyl 2-bromopropionate

生成物 1

HCID 199806952-Allyl-3-methylsuccinic acid収率 96%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2e09f620998b4121b9648bda659f5ebe
出典データセット
uspto-grants-1983_07
特許番号
US04393220

反応ノート

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