ChemicalBook CAS DataBase List Ethyl 4-(benzyloxy)-3-hydroxybenzoate

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

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177429-27-5

Step 9a: Synthesis of ethyl 4-(benzyloxy)-3-hydroxybenzoate (compound 502) A mixture of ethyl 3,4-dihydroxybenzoate (9.1 g, 50 mmol), benzyl chloride (6.3 g, 50 mmol), potassium iodide (1.66 g, 10 mmol) and potassium carbonate (13.8 g, 100 mmol) in acetonitrile (250 mL) was reacted by stirring at 40 °C overnight. Upon completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10:1, v/v) as eluent to give the title compound 502 as a white solid (4.4 g, 33% yield). LCMS (m/z): 273 [M+1]+. 1H NMR (DMSO-d6): δ 9.49 (s, 1H), 7.35 (m, 7H), 7.08 (d, J = 7.8 Hz, 1H), 5.16 (s, 2H), 4.21 (m, 2H), 1.26 (t, J = 7.5 Hz, 3H).

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

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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

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