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Dimethylformamide → Methyl 4-Benzoyl-3-hydroxyphenoxyacetate

HRID 1493414
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HRID 1493414 반응식
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(O)C>[C:4]([C:3]1[CH:12]=[CH:13][C:14]([O:16][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][C:2]=1[OH:1])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 85722,4-DihydroxybenzophenoneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

생성물 1

HCID 14618907Methyl 4-Benzoyl-3-hydroxyphenoxyacetate수율 69%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
25 °C

실험 절차

A mixture of 15.0 g (70.0 mmol) of 2,4-dihydroxybenzophenone, 10.7 g (70 mmol) of methyl bromoacetate, 19.3 g (0.14 mol) of potassium carbonate, and 125 ml of N,N-dimethylformamide is stirred at 25° C. for 18 hours. The reaction mixture is partitioned between diethyl ether and 0.5 N hydrochloric acid. Solids are removed by filtration, and the filtrate is dried over magnesium sulfate and concentrated. The concentrate is partially dissolved in diethyl ether, and solids are removed by filtration. The solid material is recrystallized from dichloromethane: 2-propanol to afford 13.7 g (69% yield) of the title compound, a pale yellow solid, mp 131°-4° C.

후처리

  1. customThe reaction mixture is partitioned between diethyl ether and 0.5 N hydrochloric acid
  2. customSolids are removed by filtration
  3. dry with materialthe filtrate is dried over magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe concentrate is partially dissolved in diethyl ether
  6. customsolids are removed by filtration
  7. customThe solid material is recrystallized from dichloromethane

출처 및 근거

ORD 기록
ord-7c11d4a2427e41058ea5fcbcb5819b06
출처 데이터셋
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05021478

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