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

HRID 2049820노트

반응식

HRID 2049820 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 241Benzene용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-0c164e7d5b9d4ef9b7336cabf448fb67
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04198527

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