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ChemicalBook CAS DataBase List 4-BENZYLOXY-2-METHOXY-BENZOIC ACID METHYL ESTER
28478-45-7

4-BENZYLOXY-2-METHOXY-BENZOIC ACID METHYL ESTER synthesis

6synthesis methods
-

Yield:28478-45-7 99.5%

Reaction Conditions:

Stage #1: methyl 2-hydroxy-4-benzyloxybenzoatewith sodium hydride in N,N-dimethyl-formamide at 0; for 0.166667 h;
Stage #2: methyl iodide in N,N-dimethyl-formamide at 0 - 20; for 17 h;

Steps:

52.B

[00186] To a solution of compound b (4.57 g, 17.7 mmol) in anhydrous DMF (70 mL) at 00C was added sodium hydride (60% dispersion in oil, 1.06 g, 26.6 mmol) EPO portionwise and the resulting mixture was stirred at 00C for 10 min. At this time, iodomethane (2.80 mL, 45 mmol) was added dropwise followed by stirring at 00C for 1 h and at rt for 16 h. The mixture was quenched with ice water (300 mL) and the solids were collected by vacuum filtration after 1 h. The solids were washed with water and dried in vacuo to give 4.80 g (99.5%) of compound b as a white solid. This material was used without any further purification. HPLC Ret. Time: 3.38 min. LCMS MH+ (m/z) 273.

References:

WO2008/57775,2008,A2 Location in patent:Page/Page column 67-68

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