1-Bromopropane → N-[4-(1-Hydroxybutyl)phenyl]acetamide

HRID 1886340Notes

Reaction equation

HRID 1886340 reaction equation
Br[CH2:2][CH2:3][CH3:4].[Mg].[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1)=[O:7].[Cl-].[NH4+]>O1CCCC1>[OH:7][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 25517Ammonium ChlorideHCID 739424-AcetamidobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 19875865N-[4-(1-Hydroxybutyl)phenyl]acetamideYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and refluxed Grignard complex previously prepared starting from 55.1 parts of 1-bromopropane, 10.9 parts of magnesium and tetrahydrofuran was added a solution of 25 parts of N-(4-formylphenyl)acetamide in 225 parts of dry tetrahydrofuran. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice water and a saturated ammonium chloride solution. The organic layer was decanted (and set aside) and the remaining phase was extracted with ethyl acetate. The combined organic layers were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 20 parts (64.3%) of N-[4-(1-hydroxybutyl)phenyl]acetamide as a residue (interm. 7).

Workup

  1. temperaturerefluxed Grignard complex
  2. custompreviously prepared
  3. stirringAfter stirring for 1 hour at room temperature
  4. customThe organic layer was decanted (and
  5. extractionwas extracted with ethyl acetate
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-d7218b8b0cd8417b81e09a5b95afa171
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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