2-(benzyloxy)-3-methoxybenzoic acid synthesis

5synthesis methods

Product Name:2-(benzyloxy)-3-methoxybenzoic acid
CAS Number:23806-76-0
Molecular formula:C15H14O4
Molecular Weight:258.27

Benzoic acid, 3-methoxy-2-(phenylmethoxy)-, phenylmethyl ester

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23806-76-0
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Yield:23806-76-0 99%

Reaction Conditions:

Stage #1: 2-Benzyloxy-3-methoxy-benzoic acid benzyl esterwith water;sodium hydroxide in methanol at 20;Inert atmosphere;
Stage #2: with hydrogenchloride in dichloromethane;water;

Steps:

To a solution of the oil (763 mg, 2.19 mmol) in 5 mL of MeOH was added 3 mL of 6M NaOH . The mixture was stirred overnight at room temperature under nitrogen. The reaction was evaporated under vacuum and the product was extracted with CH₂C1₂ and washed with 6M HC1. The organic phase was collected, dried over anhydrous MgS0₄, and concentrated under vacuum to an off-white solid (566 mg, 2.19 mmol). Yield = 99%. 1H NMR (300 MHz, CDC1₃, 25 °C): δ = 3.97 (s, 3H; OC?), 5.27 (s, 2Η; CH₂), 7.19 (d, J = 3.6 Hz, 1H; ArH), 7.36 - 7.41 (m, 5H; ArH), 7.43 (d, J = 2.1 Hz, 1H; ArH), 7.68 (dd, J = 6.3, 3.0 Hz, 1H; ArH). ESI-MS(+) m/z 259.1 1 [M+H]⁺, 276.10 [M+NH₄]⁺.

References:

WO2012/106534,2012,A2 Location in patent:Page/Page column 63