Sulfuric Acid → 5-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone

HRID 1280246

반응식

HRID 1280246 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]=[CH2:17].S(=O)(=O)(O)[OH:26]>S([O-])([O-])(=O)=O.[Hg+2].O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16](=[O:26])[CH3:17]

참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 184301613,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(2-propenyloxy)pentyloxy)benzene

생성물 1

HCID 184302155-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone수율 94%

시약·촉매·용매 2

HCID 24544Mercuric sulfate촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

A mixture of 4.12 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(2-propenyloxy)pentyloxy)benzene, 0.36 g of mercury (II) sulfate, 5 ml of 1% aqueous sulfuric acid solution, and 50 ml of tetrahydrofuran was stirred at 60° C. for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with diluted hydrochloric acid and water in this order, dried over magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 4.05 g (yield, 94%) of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone, nD25.5 1.5350.

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. additionthe filtrate was poured into diluted hydrochloric acid
  3. extractionextracted twice with diethyl ether
  4. washwashed with diluted hydrochloric acid and water in this order
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude product

출처 및 근거

ORD 기록
ord-aa0eaf858e9b47c080cf5c256cb6c62b
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448444B1

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