Diethyl methylmalonate → Propanedioic acid, 2-(3-chloro-4-nitrophenyl)-2-methyl-, 1,3-diethyl ester

HRID 261034

반응식

HRID 261034 반응식
[H-].[Na+].[CH3:3][CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:15][C:16]1[CH:21]=[C:20](Cl)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>CN(C)P(N(C)C)(N(C)C)=O.O>[CH3:3][C:4]([C:20]1[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([Cl:15])[CH:21]=1)([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

참가 물질

6

반응물 3

HCID 11857Diethyl methylmalonateHCID 118992,4-DichloronitrobenzeneHCID 24758Sodium hydride

생성물 1

HCID 12854241Propanedioic acid, 2-(3-chloro-4-nitrophenyl)-2-methyl-, 1,3-diethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 12679Hexamethylphosphoramide용매2회

실험 절차

The starting material can also be prepared as follows: 4.8 g 50% sodium hydride in mineral oil are added to 100 ml hexamethylphosphoramide while stirring under nitrogen. Hereupon 17.1 g diethyl α-methylmalonate are added and the mixture slowly heated to 100°. The solution of 19.2 g 2,4-dichloro-nitrobenzene in 20 ml hexamethylphosphoramide is added dropwise during 1/2 hour and the temperature kept at 100° for seven hours. After cooling, the mixture is diluted with water, concentrated in vacuo, the residue taken up in water and extracted with benzene. The extract is washed with water, dried, filtered, evaporated, the residue distilled and the fraction boiling at 147°-148°/0.25 mm Hg collected, to yield the diethyl α-methyl-α-(3-chloro-4-nitrophenyl)-malonate. (The analogously prepared diethyl α-ethyl-α-(3-chloro-4-nitrophenyl)-malonate boils at 170°-174°/1 mm Hg.)

후처리

  1. customThe starting material can also be prepared
  2. temperaturethe mixture slowly heated to 100°
  3. temperatureAfter cooling
  4. concentrationconcentrated in vacuo
  5. extractionextracted with benzene
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. distillationthe residue distilled
  11. customthe fraction boiling at 147°-148°/0.25 mm Hg collected

출처 및 근거

ORD 기록
ord-721bb9578c3e4c2f825b13a29fdb3719
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04163788

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