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Dimethylformamide → Methyl 4-Benzoyl-3-hydroxyphenoxyacetate

HRID 1493414
ノート
印刷プレビュー

反応式

HRID 1493414 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

HCID 14618907Methyl 4-Benzoyl-3-hydroxyphenoxyacetate収率 69%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7c11d4a2427e41058ea5fcbcb5819b06
出典データセット
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05021478

反応ノート

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