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

HRID 1915301Notes

Reaction equation

HRID 1915301 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-4a12e5f6186a4d8da723452642c5967a
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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