Pyridine → 4-Methoxycinnamic acid chloride

HRID 707735ノート

反応式

HRID 707735 の反応式
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.N1C=CC=CC=1.O=S(Cl)[Cl:22]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([Cl:22])=[O:10])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 132454-Methoxy cinnamic acidHCID 24386Thionyl Chloride

生成物 1

HCID 534017724-Methoxycinnamic acid chloride収率 94.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A first 3 L, 4 necked round bottomed flask (RBF) was equipped with a mechanical stirrer, thermowell, and a condenser with nitrogen adapter. The RBF was charged with 4-methoxycinnamic acid (175 g, 982 mmol) and 0.1 mL dry pyridine in 2 L dry toluene. The addition funnel was charged with 107.2 mL (1.473 mol) SOCl2 which was then added slowly to the reaction mixture at room temperature. The reaction mixture was heated to reflux and monitored by GC analysis (aliquots were withdrawn periodically, quenched with MeOH, and analyzed). After 5 hours, the GC analysis indicated that the reaction was complete and the reaction mixture was allowed to cool to room temperature. Excess SOCl2 and toluene were removed by rotary evaporation and the crude product was purified by distillation to give 182 g of 4-methoxycinnamoyl chloride (94% yield) with 98.9% purity by GC.

後処理

  1. customA first 3 L, 4 necked round bottomed flask (RBF) was equipped with a mechanical stirrer
  2. additionwas then added slowly to the reaction mixture at room temperature
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. customwere withdrawn periodically
  6. customquenched with MeOH
  7. customExcess SOCl2 and toluene were removed by rotary evaporation
  8. distillationthe crude product was purified by distillation

出典と根拠

ORDレコード
ord-1c3347ca8f964996a97f97d05fd92ac0
出典データセット
uspto-grants-2015_11
特許番号
US09175123B2

反応ノート

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