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

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

6synthesis methods

Product Name:4-BENZYLOXY-2-METHOXY-BENZOIC ACID METHYL ESTER
CAS Number:28478-45-7
Molecular formula:C16H16O4
Molecular Weight:272.3

5427-29-2 Synthesis

methyl 2-hydroxy-4-phenylmethoxy-benzoate

5427-29-2
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74-88-4
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4-BENZYLOXY-2-METHOXY-BENZOIC ACID METHYL ESTER

28478-45-7
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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

2150-47-2 Synthesis