5,6-Dimethyl-2-benzofuran-1,3-dione → HCID 23084580, compound

HRID 2111640Notes

Reaction equation

HRID 2111640 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][C:12]=1[CH3:13].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][C:12]=1[CH3:13])[C:6](=[O:7])[O:8][CH:9]2[OH:10]

Participants

4

Reactant 2

HCID 2266445,6-Dimethyl-2-benzofuran-1,3-dioneHCID 16721206HCID 16721206, compound

Product 1

HCID 23084580HCID 23084580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4,5-dimethylphthalic anhydride (1.5 g, 8.5 mmol) in anhydrous tetrahydrofuran (25 ml) was added a 1.0 mol/L solution of tri-tert-butoxy aluminohydride in anhydrous tetrahydrofuran (8.5 ml) under ice cooling and argon atmosphere, and stirred for 1 hr under ice cooling. To the reaction solution was added ice-cold water, and the insoluble materials was filtered off. The filtrate was concentrated under reduced pressure to give crude 5,6-dimethyl-3-hydroxyphthalide. To this was added methyl iodide (12 g, 85 mmol) and K2CO3 (9.4 g, 68 mmol), and heated under reflux in acetone solvent for 5 hrs. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform) to give 0.64 g of methyl 4,5-dimethyl-2-formylbenzoate.

Workup

  1. additionTo the reaction solution was added ice-cold water
  2. filtrationthe insoluble materials was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-08c50a08cf9b4e7799b582d170a3c836
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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