Reaction #2689

Reaction equation

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic acid

Potassium carbonate

methyl iodide

→

pure product

Yield 88.3%

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic acid methyl ester

Yield 88.3%

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureAfter cooling to ambient temperature
2. 2
   FiltrationThe precipitate was filtered off
3. 3
   Otherthe solution was evaporated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in saturated aqueous NaHCO3
5. 5
   Dryingthe organic phase was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated

Procedure

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic acid (10.0 g, 38.0 mmol) was dissolved in dry DMF (100 mL). Potassium carbonate (15.2 g, 110.0 mmol) was added and the reaction was heated to 55° C. for 30 min. After cooling to ambient temperature, methyl iodide (15.6 g, 110.0 mmol) was added and the solution was stirred overnight. The precipitate was filtered off and the solution was evaporated. The residue was dissolved in saturated aqueous NaHCO3 and ether. The aqueous layer was discarded and the organic phase was dried (Na2SO4), filtered and evaporated to give 9.4 g (88%) of the pure product.

Source