2-Bromoethanol → 2-(3-Methyl-4-nitrophenoxy)ethanol

HRID 402638

反応式

HRID 402638 の反応式
[N+:1]([C:4]1[C:5]([CH3:11])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[O:10][CH2:13][CH2:14][OH:15]

参加物

5

反応物 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 174123-Methyl-4-nitrophenol

生成物 1

HCID 100585272-(3-Methyl-4-nitrophenoxy)ethanol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A solution of 4-nitro-m-cresol (1.4 g, 9.4 mmol), 2-bromoethanol (1.0 mL, 0.014 mol) and potassium carbonate (3.3 g, 0.024 mol) in N,N-dimethylformamide (10 mL) was stirred with heating at 70° C. for 12 h. Cooled to ambient temperature, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel(hexane/ethyl acetate) to afford 2-(3-methyl-4-nitrophenoxy)ethanol as solid (1.3 g, y. 70%).

後処理

  1. temperatureCooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel(hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-20342ab64b3b48afb38ac10084bfa11c
出典データセット
uspto-grants-2014_06
特許番号
US08742113B2

関連ノート

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