HCID 14772476, compound → N-(1,1-Dimethyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl)acetamide

HRID 1084471Notes

Reaction equation

HRID 1084471 reaction equation
[CH3:1][C:2]([OH:16])([CH3:15])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][C:10]([CH3:12])=[O:11])[C:4]=1[CH2:13][OH:14]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:15][C:2]1([CH3:1])[C:3]2[C:4](=[C:5]([NH:9][C:10]([CH3:12])=[O:11])[CH:6]=[CH:7][CH:8]=2)[C:13](=[O:14])[O:16]1

Participants

4

Reactant 1

HCID 14772476HCID 14772476, compound

Product 1

HCID 14772477N-(1,1-Dimethyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl)acetamideYield 62.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 7.2 g of α,α-dimethyl-2-hydroxymethyl-3-acetaminobenzyl alcohol in 300 ml of chloroform was added 28 g of activated manganese dioxide and the mixture was allowed to react for 6 hours under refluxing. After the reaction was over, the reaction mixture was left to stand for cooling and filtered on a glass filter having a bed of celite. The residue was washed with 100 ml of chloroform. The filtrate and the washed solution were combined and concentrated to obtain an oily substance. The oily substance was purified by silica gel column chromatography to obtain 4.4 g of 3,3-dimethyl-7-acetaminophthalide in the white crystal form. m.p. 124.1 ° C.

Workup

  1. customto react for 6 hours
  2. temperatureunder refluxing
  3. waitwas left
  4. temperaturefor cooling
  5. filtrationfiltered on a glass
  6. filtrationfilter
  7. washThe residue was washed with 100 ml of chloroform
  8. concentrationconcentrated
  9. customto obtain an oily substance
  10. customThe oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dcdbdc042639430eb30ce948f02bab92
Source dataset
uspto-grants-1991_04
Patent number
US05004816

Reaction notes

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