Ethyl 4-(benzyloxy)-3-hydroxybenzoate synthesis

11synthesis methods

Product Name:Ethyl 4-(benzyloxy)-3-hydroxybenzoate
CAS Number:177429-27-5
Molecular formula:C16H16O4
Molecular Weight:272.3

Benzoic acid, 3-(acetyloxy)-4-(phenylmethoxy)-, ethyl ester

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177429-27-5
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Yield:177429-27-5 96%

Reaction Conditions:

with water;sodium carbonate in tetrahydrofuran;methanol at 20;Inert atmosphere;

Steps:

3.3.3. Ethyl 3-hydroxy-4-benzyloxybenzoate (4d)

Compound 7 (2.00 g, 6.36 mmol) was dissolved in MeOH/THF (2:1, 45 mL). A solution of sodium carbonate (0.81 g. 7.64 mmol in 15 mL of H₂O) was added. The mixture was stirred overnight at room temperature and then concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine and dried (MgSO₄). Solvent removal under vacuum gave the product as a white solid (1.66 g, 96%); mp 82-84 °C; ν_max (KBr disc, cm^-1) 3383 (OH), 1686 (CO); δ_H (400 MHz, CDCl₃) 7.63 (d, 1H, J 1.9 Hz, H-2); 7.61 (dd, 1H, J 1.9, 8.3 Hz, H-6), 7.45-7.35 (5H, m, Bn H), 6.95 (d, 1H, J 8.3 Hz, H-5), 5.70 (br s, 1H, OH), 5.18 (s, 2H, Bn CH₂), 4.35 (q, 2H, J 7.1 Hz, CH₂CH₃), 1.40 (t, 3H, J 7.1 Hz, CH₃); δ_C (100.6 MHz, CDCl₃) 149.9, 145.4, 135.6, 128.9, 128.7, 127.9, 124.1, 122.6, 115.8, 111.2, 71.1, 60.8, 14.4; m/z (ESI⁺) 295 [M+Na]⁺, HRESI⁺ 295.0945, C₁₆H₁₆NaO₄ requires 295.0946.

References:

Zhang, Qingzhi;Raheem, K. Saki;Botting, Nigel P.;Slawin, Alexandra M.Z.;Kay, Colin D.;O'Hagan, David [Tetrahedron,2012,vol. 68,# 22,p. 4194 - 4201] Location in patent:experimental part

3943-89-3 Synthesis