Hydrochloric Acid → 1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester

HRID 599716ノート

反応式

HRID 599716 の反応式
C[O-].[Na+].[C:4](OC)(=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH2:13]([C:18]1C(=O)[CH2:20][CH2:21][C:22]=1[O:23]C)[CH2:14][CH2:15][CH2:16][CH3:17].Cl>CO>[CH3:9][O:8][C:6](=[O:7])[CH2:5][C:4]1[CH2:20][CH2:21][C:22](=[O:23])[C:18]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 167262722-Pentyl-3-methoxy-2-cyclopentenone

生成物 1

HCID 906341-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

反応条件

温度
25 °C

実験手順

The air in a reactor (a volume of 0.3 L) was preliminarily replaced with nitrogen at ordinary pressure. The reactor was charged with 13.5 g (70 mmol) of a 28% methanol solution of sodium methoxide and 140 ml of absolute methanol. Thereto was added 6.6 g (50 mmol) of dimethyl malonate, and the mixture was stirred for 30 minutes at 25° C. Thereto was added 6.6 g (36 mmol) of 2-pentyl-3-methoxy-2-cyclopentenone, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. The resulting mixture was ice-cooled and neutralized by gradually adding 6.1 ml of concentrated hydrochloric acid, and methanol was distilled off. Thereto were added 50 ml of water and 100 ml of toluene, and then the mixture was stirred sufficiently and allowed to stand to separate the organic phase. The toluene in the organic phase was distilled off in vacuo followed by vacuum distillation, yielding methyl(2-pentyl-3-keto-1-cyclopentenyl-)acetate (a compound in which R22 represents an n-pentyl group, and R23 represents a methyl group in the above formula (15)). Gas chromatographic analysis showed that the yield of methyl(2-pentyl-3-keto-1-cyclopentenyl-)acetate relative to 2-pentyl-3-methoxy-2-cyclopentenone was 90%.

後処理

  1. customThe air in a reactor (a volume of 0.3 L) was preliminarily replaced with nitrogen at ordinary pressure
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 24 hours in a nitrogen atmosphere
  4. temperaturecooled
  5. distillationwas distilled off
  6. additionThereto were added 50 ml of water and 100 ml of toluene
  7. stirringthe mixture was stirred sufficiently
  8. customto separate the organic phase
  9. distillationThe toluene in the organic phase was distilled off in vacuo
  10. distillationfollowed by vacuum distillation

出典と根拠

ORDレコード
ord-74366ef3970646e9ba2cf3917cedd432
出典データセット
uspto-grants-2011_03
特許番号
US07897802B2

反応ノート

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