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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 496722Generated: October 30, 2026

Methyl iodide → Methyl 5-acetyl-2-methoxybenzoate

https://huagongshe.com/reaction/496722

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantCesium carbonateHCID 10796—
ReactantMethyl 5-acetylsalicylateHCID 85444—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductMethyl 5-acetyl-2-methoxybenzoateHCID 606426—

Reaction Conditions

Temperature0 °C

Reaction Steps

To a stirred solution of Methyl 2-hydroxy-5-acetylbenzoate (12 g, 61.7 mmol) in DMF (200 ml) was added cesium carbonate (24.15 g, 74.1 mmol) and MeI (9.64 g, 68 mmol). The reaction mixture was stirred for 16 hours at 0° C. and then diluted with ethyl acetate, washed with aq Na2S2O5, brine, dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on silica gel column (ethyl acetate:hexane 1:2) to provide the title compound as an off white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06946491B2
Source datasetuspto-grants-2005_09
ORD IDord-af232c2f018f4e629ce66b9750dd9680
Source noteuspto-grants-2005_09