HCID 15036289, compound → HCID 15036290, compound

HRID 728580Notes

Reaction equation

HRID 728580 reaction equation
[CH2:1]([C:3]([OH:18])([CH2:16][CH3:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([CH3:13])=[O:12])[C:5]=1[CH2:14][OH:15])[CH3:2]>O1CCCC1.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1([CH2:16][CH3:17])[C:4]2[C:5](=[C:6]([NH:10][C:11]([CH3:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[C:14](=[O:15])[O:18]1)[CH3:2]

Participants

4

Reactant 1

HCID 15036289HCID 15036289, compound

Product 1

HCID 15036290HCID 15036290, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.0 g of α,α-diethyl-2-hydroxymethyl-3-acetaminobenzyl alcohol in 300 ml of tetrahydrofuran was added 32 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 tetrahydrofuran. 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 4.9 g of 3,3-diethyl-7-acetaminophthalide in the colorless oily substance.

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 tetrahydrofuran
  8. concentrationconcentrated
  9. customto obtain an oily substance
  10. customThe oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bf1d55aca83741958100901949f36cb8
Source dataset
uspto-grants-1991_09
Patent number
US05049575

Reaction notes

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