Dichloromethane → 2-methoxy-4-[(E)2-methoxycarbonyl-vinyl]phenyl 4-(3-butenyloxy)benzoate

HRID 1739495ノート

反応式

HRID 1739495 の反応式
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].S(Cl)(Cl)=O.O[C:20]1[CH:31]=[CH:30][C:23](/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:21]=1[O:32][CH3:33].C(Cl)Cl>CN(C)C=O.C(N(CC)CC)C>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][C:20]2[CH:31]=[CH:30][C:23](/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:21]=2[O:32][CH3:33])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 5444524-(3-Butenyloxy)benzoic acidHCID 5357283Methyl Ferulate

生成物 1

HCID 218413722-methoxy-4-[(E)2-methoxycarbonyl-vinyl]phenyl 4-(3-butenyloxy)benzoate収率 76.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 8471Triethylamine溶媒

実験手順

A mixture of 4.85 g of 4-(3-butenyloxy)benzoic acid and 6 ml of thionyl chloride was treated with 3 drops of dimethylformamide and heated to reflux for 3 hrs. The excess acid chloride was thereupon distilled off firstly at normal pressure and then with increasing vacuum, the residue was held under a high vacuum for 2.5 hrs. and subsequently dissolved in 20 ml of methylene chloride. This solution was added dropwise while cooling with ice to obtain a mixture of 5 g of methyl (E)-4-hydroxy-3-methoxycinnamate, 25 ml of methylene chloride and 3.9 ml of triethylamine and subsequently left to react at room temperature for 60 hrs. Then, the reaction solution was filtered, concentrated slightly and chromatographed over 314 g of silica gel with methylene chloride. Crystallization from cold ethanol gave 7.03 g of 2-methoxy-4-[(E)2-methoxycarbonyl-vinyl]phenyl 4-(3-butenyloxy)benzoate.

後処理

  1. temperatureheated
  2. temperatureto reflux for 3 hrs
  3. distillationThe excess acid chloride was thereupon distilled off firstly at normal pressure
  4. temperaturewith increasing vacuum
  5. dissolutionand subsequently dissolved in 20 ml of methylene chloride
  6. additionThis solution was added dropwise
  7. temperaturewhile cooling with ice
  8. customto obtain
  9. waitsubsequently left
  10. customto react at room temperature for 60 hrs
  11. filtrationThen, the reaction solution was filtered
  12. concentrationconcentrated slightly
  13. customchromatographed over 314 g of silica gel with methylene chloride
  14. customCrystallization from cold ethanol

出典と根拠

ORDレコード
ord-79a0a3d61c884d6c82cb871a0c939b46
出典データセット
uspto-grants-1999_10
特許番号
US05965761

反応ノート

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