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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1646991Generated: October 27, 2026

Diethyl Ether → 6-chloro-2-methyl-3(2H)-benzofuranone

https://huagongshe.com/reaction/1646991

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantSodium hydrideHCID 24758—
ReactantAmmonium ChlorideHCID 25517—
Reactant4-Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl esterHCID 86746513—
SolventTetrahydrofuranHCID 8028—
Product6-chloro-2-methyl-3(2H)-benzofuranoneHCID 1938468844.4%

Reaction Steps

A mixture of the compound of Example 7, Step A, (6.7 g) and sodium hydride (60% in oil, 1.5 g) was heated to reflux in tetrahydrofuran (50 ml). It was then allowed to cool to room temperature over 1.5 hrs. The cooled mixture was treated with aqueous ammonium chloride solution and ether. The ether solution was dried over magnesium sulfate and then evaporated. The oil was subjected to chromatography on silica gel with hexanes/ethyl acetate (25:1) as the eluent. The desired product (1.99 g) was obtained as a low melting solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05182303
Source datasetuspto-grants-1993_01
ORD IDord-a19b54bb239a4dd093ae862319d1b5ea
Source noteuspto-grants-1993_01