Reaction #50476

Reaction equation

compound

4- Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl ester

sodium hydride

ammonium chloride

ether

→

desired product

Yield 44.4%

6-chloro-2-methyl-3(2H)-benzofuranone

Yield 44.4%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   DryingThe ether solution was dried over magnesium sulfate
3. 3
   Otherevaporated

Procedure

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. NMR: 7.6 (d, 1H), 7.1 (m 2H), 4.7 (q, 1H), 1.55 (d, 3H).

Source