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

HRID 253239

Reaction equation

HRID 253239 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-15bf665e3cb3497ea8c928521ee0839c
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Linked notes

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