Water → N-(4,4-dimethyl-chroman-7-yl)-acetamide

HRID 1727542Notes

Reaction equation

HRID 1727542 reaction equation
[CH3:1][C:2](=[CH2:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>FC1C=CC=CC=1>[CH3:16][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 57567384N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide

Product 1

HCID 57470214N-(4,4-dimethyl-chroman-7-yl)-acetamideYield 54%

Reagents, catalysts & solvents 1

HCID 10008FluorobenzeneSolvent

Procedure

A mixture of N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide (2.5 g, 11.4 mmol) and AlCl3 (4.52 g, 34.3 mmol) in fluoro-benzene (50 mL) was heated at reflux overnight. After cooling, the reaction mixture was poured into water. The organic layer was separated and the aqueous phase was extracted with EtOAc (40×3 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give N-(4,4-dimethyl-chroman-7-yl)-acetamide (1.35 g, 54%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with EtOAc (40×3 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2402ee03358b4b5d84bdf6a314735d53
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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