Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 326293Generated: October 27, 2026

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

https://huagongshe.com/reaction/326293

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 numberUS05268388
Source datasetuspto-grants-1993_12
ORD IDord-9635379bfccc45df8e73c298b9ffafad
Source noteuspto-grants-1993_12