Acetophenone → HCID 18690517、化合物

HRID 1872444ノート

反応式

HRID 1872444 の反応式
[H-].[Na+].[C:3]([O:12]C)(=O)[CH2:4][CH2:5][CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(O)(=O)CCCC(C)(C)C.[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])[CH3:25]>C1(C)C(C)=CC=CC=1>[C:27]1([C:24](=[O:26])[CH2:25][C:3]([CH2:4][CH2:5][CH2:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:12])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 7410AcetophenoneHCID 24758Sodium hydrideHCID 30151835,5-Dimethylhexanoic acidHCID 18690527HCID 18690527、化合物

生成物 1

HCID 18690517HCID 18690517、化合物収率 53%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒2 回

反応条件

温度
135 °C

実験手順

A 500 mL, 4 neck round bottom flask equipped with mechanical stirring, a nitrogen inlet, a thermometer, a condenser and an addition funnel was charged with 60% sodium hydride in mineral oil (20.5 g. 0.51 mol), methyl neo-octanoate (92.3 g., 0.58 mol, prepared from neo-octanoic acid, a product of Exxon), and xylene (42.8 g.). The mixture was heated to reflux (135° C.), and then a solution of acetophenone (32.4 g. 0.27 mol) in xylene (19.1 g.) was added over 1.25 h. The mixture was kept at reflux for an additional 1 h. After cooling to room temperature, the reaction was quenched by the careful addition of methanol (20 mL), and then acidified with 150 g/L sulfuric acid (180 mL). After separation of layers, the organic phase was washed with water (2×100 mL) and brine (100 mL). After drying by passing through anhydrous sodium sulfate, the solution was concentrated in vacuo at 70° C. down to 12 mbar to yield an orange liquid containing product in a crude yield of 63%. Vacuum distillation (200 mtorr) through a 15 cm Vigreux column yielded the product in the heart cut: 1-phenyl-3-neoheptyl-1,3-propanedione (X) (37.2 g., 96% pure, 0.14 mol; 53% yield; bp: 94-135° C.). Dypnone, the self-condensation product of acetophenone was undetectable in the product.

後処理

  1. customA 500 mL, 4 neck round bottom flask equipped with mechanical stirring, a nitrogen inlet
  2. temperatureThe mixture was heated
  3. temperatureat reflux for an additional 1 h
  4. temperatureAfter cooling to room temperature
  5. customthe reaction was quenched by the careful addition of methanol (20 mL)
  6. customAfter separation of layers
  7. washthe organic phase was washed with water (2×100 mL) and brine (100 mL)
  8. customAfter drying
  9. concentrationthe solution was concentrated in vacuo at 70° C. down to 12 mbar
  10. customto yield an orange liquid
  11. additioncontaining product in a crude yield of 63%
  12. distillationVacuum distillation (200 mtorr) through a 15 cm Vigreux column
  13. customyielded the product in the heart cut

出典と根拠

ORDレコード
ord-a8c6d292fba9485da03ee8f3315adb43
出典データセット
uspto-grants-2000_08
特許番号
US06107523

反応ノート

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