Benzoic acid, 4-(hydroxyMethyl)-3-Methoxy-, Methyl ester synthesis
- Product Name:Benzoic acid, 4-(hydroxyMethyl)-3-Methoxy-, Methyl ester
- CAS Number:79236-96-7
- Molecular formula:C10H12O4
- Molecular Weight:196.2
70264-94-7
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Yield:79236-96-7 52.3%
Reaction Conditions:
with water;sodium hydrogencarbonate;tetrabutylammomium bromide at 20 - 70; for 5 h;
Steps:
55.B
To a suspension of methyl 4-(bromomethyl)-3-methoxybenzoate (1 g, 3.9 mmol) in water (35 ml.) was added n-Bu4NBr (0.2 g, 0.624 mmol) and NaHCO3 (3.5 g, 42 mmol) at rt. The reaction mixture was heated to 70 0C and stirred for 5 h. The resulting solution was acidified with aqueous HCI (2 mol/L) and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give the product of Step B (0.4 g, 52.3 %): 1H NMR (CDCI3, 300 MHz) δ 7.62 (dd, J = 1 1.7 and 12.6 Hz, 1 H), 7.57 (s, 1 H), 7.46 (dd, J= 0.9 and 4.5 Hz, 1 H), 4.66(s, 2 H), and 3.85 (s, 6 H).
References:
WO2009/32667,2009,A1 Location in patent:Page/Page column 180
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3556-83-0
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