Methyl iodide → 4-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

To a solution of 4-hydroxy-isobenzofuran-1,3-dione (195 mg, 1.2 mmol) in anhydrous N,N-dimethylformamide (4 ml) under nitrogen was added sodium hydride (61 mg, 1.56 mmol). The solution was stirred for 15 minutes and then methyl iodide (0.37 ml, 6.0 mmol) was added. The reaction was stirred for 48 hours and then quenched with saturated ammonium chloride. The mixture was concentrated in vacuo, diluted in ethyl acetate (20 ml) and the organic phase washed with 1N hydrochloric acid (5 ml) and brine (3×5 ml). The organic layer was dried (MgSO4) and concentrated in vacuo. To the crude solid was added methanol causing a precipitate to form. The flask was cooled in an ice bath for 2 hours and the solid filtered off, washed with methanol and dried in vacuo which afforded 0.1 g (47%) of 4-methoxy-isobenzofuran-1,3-dione as a solid.

1. stirringThe reaction was stirred for 48 hours
2. customquenched with saturated ammonium chloride
3. concentrationThe mixture was concentrated in vacuo
4. additiondiluted in ethyl acetate (20 ml)
5. washthe organic phase washed with 1N hydrochloric acid (5 ml) and brine (3×5 ml)
6. dry with materialThe organic layer was dried (MgSO4)
7. concentrationconcentrated in vacuo
8. additionTo the crude solid was added methanol causing a precipitate
9. customto form
10. temperatureThe flask was cooled in an ice bath for 2 hours
11. filtrationthe solid filtered off
12. washwashed with methanol
13. customdried in vacuo which

ORD record

ord-ffe6c1ebe8bc47eab4d68da3ddcd4e8f

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07019026B1