Water → m-Phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

HRID 2049820ノート

反応式

HRID 2049820 の反応式
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:9]([C:10]([OH:12])=[O:11])[C:8]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[O:21]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C.C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH2:31][C:30]3[CH:33]=[CH:34][CH:35]=[C:28]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:29]=3)=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1

参加物

8

反応物 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 262953-Phenoxybenzyl alcoholHCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

生成物 1

HCID 20344538m-Phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 241Benzene溶媒

実験手順

A mixture of 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (0.95 g, 3,95 mmol), thionyl chloride (0.342 ml, 4.74 mmol) and DMF (several drops) in 50 ml benzene is stirred at RT for 2 days. The solvent and excess thionyl chloride are evaporated under reduced pressure. The resulting acid chloride is dissolved in 50 ml benzene, and 0.79 g m-phenoxybenzyl alcohol (3.95 mmol) and 0.482 g 4-dimethylaminopyridine (3.95 mmol) are added. The mixture is left at 25° for 18 hr and then heated under reflux for 2 hr. The mixture is then poured into water and extracted with ether. The organic phase is washed with dilute HCl, sat.NaHC3, water and brine, dried and concentrated under vacuum. The crude product is purified by preparative TLC developing with 20% ethyl acetate/hexane to yield m-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate, MS m/e 422 [M+].

後処理

  1. customThe solvent and excess thionyl chloride are evaporated under reduced pressure
  2. dissolutionThe resulting acid chloride is dissolved in 50 ml benzene
  3. waitThe mixture is left at 25° for 18 hr
  4. temperatureheated
  5. temperatureunder reflux for 2 hr
  6. extractionextracted with ether
  7. washThe organic phase is washed with dilute HCl
  8. dry with materialNaHC3, water and brine, dried
  9. concentrationconcentrated under vacuum
  10. customThe crude product is purified by preparative TLC

出典と根拠

ORDレコード
ord-0c164e7d5b9d4ef9b7336cabf448fb67
出典データセット
uspto-grants-1980_04
特許番号
US04198527

反応ノート

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