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Water → 2-(4-Chlorophenoxy)-1-(4-chlorophenyl)-2-methylpropan-1-one

HRID 1638375
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HRID 1638375 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25](Br)([CH3:27])[CH3:26])=[O:24])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:25]([C:23]([C:20]2[CH:19]=[CH:18][C:17]([Cl:16])=[CH:22][CH:21]=2)=[O:24])([CH3:27])[CH3:26])=[CH:4][CH:3]=1
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반응물 4

HCID 962Water2회HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 112999732-Bromo-1-(4-chlorophenyl)-2-methylpropan-1-one

생성물 1

HCID 198424902-(4-Chlorophenoxy)-1-(4-chlorophenyl)-2-methylpropan-1-one수율 85%

시약·촉매·용매 1

HCID 1140
Toluene
용매
2회

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온도
40 °C

실험 절차

A solution of 59.2 g (0.47 mol) of dimethyl sulphate and 32 g (0.517 mol) of dimethyl sulphide in 270 ml of acetonitrile is stirred at room temperature for 5 days. A solution of 87 g of 4-chlorophenyl 2-(p-chlorophenoxy)-prop-2-yl ketone in 80 ml of acetonitrile is then added dropwise at 20° to 25° C., in the course of approx. 2 hours. 28.7 g (0.53 mol) of sodium methylate are introduced at the same temperature, and the mixture is stirred for a further 12 hours and then concentrated. The residue is stirred overnight with a mixture of 200 ml of ethyl acetate and 150 ml of water. The organic phase is separated off, dried over sodium sulphate and concentrated in vacuo. 49 g (76% of theory) of crude 2-(4 chlorophenyl)-2-[2-(p-chlorophenoxy)-prop-2-yl]-oxirane are obtained, and this compound is directly reacted further. ##STR158## 52 g (0.3982 mol) of p-chlorophenol and 55 g (0.3982 mol) of potassium carbonate in 400 ml of toluene are heated under reflux for 2 hours in a water separator. The mixture is cooled to 40° C., and a solution of 2-bromo-prop-2-yl 4-chlorophenyl ketone in 170 ml of toluene is added dropwise. This reaction mixture is stirred for a further 5 hours at 100° C. and then cooled, water is added and the organic phase is separated off. This is washed with dilute sodium hydroxide solution and water, dried over sodium sulphate and concentrated. 87 g (85% of theory) of crude 4-chlorophenyl 2-(p-chlorophenoxy)-prop-2-yl ketone are obtained, and this compound is directly reacted further. ##STR159## 1 ml of hydrogen bromide/glacial acetic acid is added to 65.5 g (0.36 mol) of 4-chlorophenyl isopropyl ketone in 200 ml of chloroform, and 57.5 g (0.36 mol) of bromine are then added dropwise at 30° C. The mixture is stirred for a further 30 minutes at room temperature, and thereafter concentrated in vacuo. 86.6 g (92% of theory) of crude 2-bromo-prop-2-yl 4-chlorophenyl ketone are obtained, and this compound is directly reacted further.

후처리

  1. customthis compound is directly reacted further
  2. temperaturecooled
  3. customthe organic phase is separated off
  4. washThis is washed with dilute sodium hydroxide solution and water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-21e9cd1b48c548c2bc5065885796707b
출처 데이터셋
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04879385

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