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

HRID 253239

반응식

HRID 253239 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-15bf665e3cb3497ea8c928521ee0839c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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