Methyl 4-(benzyloxy)-3-hydroxybenzoate synthesis

5synthesis methods

Product Name:Methyl 4-(benzyloxy)-3-hydroxybenzoate
CAS Number:87687-75-0
Molecular formula:C15H14O4
Molecular Weight:258.27

2150-43-8 Synthesis

2150-43-8
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100-39-0
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Yield:87687-75-0 78%

Reaction Conditions:

with hydrogen;potassium carbonate in acetonitrile at 80; for 12 h;

Steps:

23.1 Step 1: Methyl 4-benzyloxy-3-hydroxy-benzoate

To a solution of methyl 3, 4-dihydroxybenzoate (10.00 g, 59.47 mmol, 1.00 eq) and potassium carbonate (8.22 g, 59.47 mmol, 1.00 eq) in acetonitrile (120 niL) was added benzyl bromide (10.17 g, 59.47 mmol, 7.06 niL, 1.00 eq). The mixture was stirred at 80 °C for 12 h under hydrogen atmosphere. LCMS showed that the reaction was completed. The mixture was filtered. The filtrate was concentrated under reduced pressure to give the residue. The residue was diluted with water (100 ml.) and extracted with dichloromethane (200 ml,). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate = 20: 1 to 10: 1) to give methyl 4-benzyloxy-3 -hydroxy-benzoate (12.00 g, 46.46 mmol, 78% yield) as a white solid. LCMS: MS (ESI) m/z: 259.1[M+1] ⁺. T-I NMR: (400 MHz, CDCb)5:7.69 - 7.57 (m, 2 H), 7.50 - 7.35 (m, 5 H), 6.97 (d, i 8.4 Hz, 1 H), 5.82 - 5.70 (m, 1 H), 5.19 (s, 2 H), 3.94 - 3.84 (m, 3 H). Chemical Formula: C15H14O4, Molecular Weight: 258.27

References:

WO2021/127443,2021,A1 Location in patent:Paragraph 0781-0787

2150-43-8 Synthesis

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100-51-6 Synthesis