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ChemicalBook CAS DataBase List Methyl salicylate
119-36-8

Methyl salicylate synthesis

15synthesis methods
Methyl salicylate can be produced by esterifying salicylic acid with methanol. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Betula lenta (sweet birch) and Gaultheria procumbens (eastern teaberry or winter green).
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Yield:119-36-8 98%

Reaction Conditions:

with sulfuric acid for 20 h;Reflux;

Steps:

2.1

H2SO4 (4.0 mL, 74.63 mmol) was added to a solution of salicylic acid (5.0 g, 36.20 mmol) in MeOH (60 mL). The reaction mixture was refluxed for 20 h, allowed to reach r.t., poured into H2O (100 mL) and extracted with CH2Cl2 (120 mL). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5% EtOAc/hexanes) to furnish 5.44 g of methyl 2-hydroxybenzoate (colourless oil, yield: 98%).1H NMR (CDCl3, 250 MHz) δ ppm: 10.75 (s, 1H), 7.84 (dt, J1=6.6 Hz, J2=8.2 Hz, 1H), 7.45 (m, 1H), 6.98 (d, J=8.2 Hz, 1H), 6.87 (m, 1H), 3.95 (s, 3H).

References:

US2012/149769,2012,A1 Location in patent:Page/Page column 21-22

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