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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 450885Generated: October 31, 2026

Methyl iodide → Methyl 5-acetyl-2-methoxybenzoate

https://huagongshe.com/reaction/450885

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 numberUS08487000B2
Source datasetuspto-grants-2013_07
ORD IDord-2e57aab471d944faaa1792da25d0ac80
Source noteuspto-grants-2013_07