Ethyl Acetate → Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate

HRID 253239

反応式

HRID 253239 の反応式
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][O:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].[C:24]([O:27][CH2:28]C)(=O)[CH3:25]>CN(C=O)C>[CH3:13][O:14][CH2:15][CH2:16][O:1][C:2]1[C:11]([O:12][CH2:25][CH2:24][O:27][CH3:28])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 75484Methyl 2,3-DihydroxybenzoateHCID 809722-Bromoethyl methyl ether

生成物 1

HCID 66888836Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate収率 95%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of methyl 2,3-dihydroxybenzoate (2.18 g, 12.97 mmol), 2-bromoethyl methyl ether (4.50 g, 32.42 mmol), and potassium carbonate (6.91 g, 50.0 mmol) in DMF (20 mL) was stirred at 60° C. for 16 h. The reaction mixture was diluted with ethyl acetate (300 mL), washed with 5% aqueous LiCl (2×50 mL), and brine (50 mL), dried with sodium sulfate, and concentrated to provide crude methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate (3.49 g, 95% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ7.32 (dd, 1H), 7.05 (m, 2H), 4.22 (m, 2H), 4.15 (m, 2H), 3.88 (s, 3H), 3.75 (m, 4H), 3.43 (s, 6H).

後処理

  1. washwashed with 5% aqueous LiCl (2×50 mL), and brine (50 mL)
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-15bf665e3cb3497ea8c928521ee0839c
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

関連ノート

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