Methyl iodide → 4-Methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis-(1,3)-dioxole

HRID 2593Notes

Reaction equation

HRID 2593 reaction equation
[CH3:1][C:2]1([CH3:19])[O:6][C:5]2[C:7]([C:16]([OH:18])=[O:17])=[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]3=[CH:15][C:4]=2[O:3]1.[C:20](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:20][O:17][C:16]([C:7]1[C:8]2[O:12][C:11]([CH3:13])([CH3:14])[O:10][C:9]=2[CH:15]=[C:4]2[O:3][C:2]([CH3:19])([CH3:1])[O:6][C:5]=12)=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 211891412,2,6,6-Tetramethylbenzo [1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic Acid

Product 1

HCID 206693184-Methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis-(1,3)-dioxoleYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

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.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationThe precipitate was filtered off
  3. customthe solution was evaporated
  4. dissolutionThe residue was dissolved in saturated aqueous NaHCO3
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b748cc817d6e4b11bba391ca0648edaa
Source dataset
uspto-grants-1998_03
Patent number
US05728370

Reaction notes

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