Isopropyl iodide → 2,2-dimethyl-8-(propan-2-yloxy)-4H-1,3-benzodioxin-4-one

HRID 577561Notes

Reaction equation

HRID 577561 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:13]2[O:14][C:15]([CH3:20])([CH3:19])[O:16][C:17](=[O:18])[C:12]=2[CH:11]=[CH:10][CH:9]=1.I[CH:22]([CH3:24])[CH3:23]>CN(C)C=O>[CH3:19][C:15]1([CH3:20])[O:14][C:13]2[C:8]([O:7][CH:22]([CH3:24])[CH3:23])=[CH:9][CH:10]=[CH:11][C:12]=2[C:17](=[O:18])[O:16]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 225569958-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Product 1

HCID 867237872,2-dimethyl-8-(propan-2-yloxy)-4H-1,3-benzodioxin-4-oneYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (5.46 g, 16.6 mmol) was added to a solution of 8-hydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one (123a, 1.50 g, 7.73 mmol) in N,N-dimethylformamide (31 mL) and the mixture stirred at room temperature for five minutes before 2-iodopropane (1.00 mL, 10.0 mmol) was added. The mixture was stirred at room temperature for 80 minutes, then partitioned between deionized water (30 mL) and ethyl acetate (2×75 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated under vacuum, and purified by column chromatography (ethyl acetate/heptane) to give 2,2-dimethyl-8-(propan-2-yloxy)-4H-1,3-benzodioxin-4-one (123b, 1.41 g, 77% yield) as a colorless gel which slowly crystallized to a white solid.

Workup

  1. additionwas added
  2. custompartitioned between deionized water (30 mL) and ethyl acetate (2×75 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. custompurified by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-faaf52409bbf4cbf85b391c2f8621b0d
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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