2-Bromopropane → HCID 14518423, compound

HRID 1723117Notes

Reaction equation

HRID 1723117 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[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)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 25517Ammonium ChlorideHCID 739424-AcetamidobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 14518423HCID 14518423, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(a-1) To a stirred and refluxed Grignard complex previously prepared starting from 110.7 parts of 2-bromopropane, 21.75 parts of magnesium and 900 parts of dry tetrahydrofuran were added dropwise 50 parts of N-(4-formylphenyl)acetamide at <30° C. Upon completion, stirring was continued for 1 hour at room temperature. The reaction mixture was hydrolysed with a mixture of ammonium chloride and crushed ice and the product was extracted with ethyl acetate. The extract was washed with water, dried, filtered and evaporated to dry, yielding 63.5 parts (100%) of N-[4-(1-hydroxy-2-methylpropyl)phenyl]acetamide as a residue (int. 101).

Workup

  1. temperaturerefluxed Grignard complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. customcrushed ice
  5. extractionthe product was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customto dry

Sources & evidence

ORD record
ord-f6dd09b3352d4ccf840f40a44d3e593a
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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