1-Bromopropane → HCID 18433157, compound

HRID 1376983Notes

Reaction equation

HRID 1376983 reaction equation
[H-].[Na+].[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:10]([OH:17])=[C:9]([CH3:18])[C:8]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:5])[CH3:4].[CH2:23](Br)[CH2:24][CH3:25].[Cl-].[NH4+]>CN(C)C=O>[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:11][C:10]([O:17][CH2:23][CH2:24][CH3:25])=[C:9]([CH3:18])[C:8]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22918670HCID 22918670, compound

Product 1

HCID 18433157HCID 18433157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (100 mg) was suspended in N,N-di-methylformamide (5 ml) and a solution of 4-acetoxy-3,5-di-tert-butyl-2-methylphenol (0.5 g) in N,N-dimethylformamide (5 ml) was added dropwise to the suspension at 0° C. After stirring for 20 min, propyl bromide (0.2 ml) was added and the mixture was stirred for an additional 2 h. The reaction mixture was then poured into a saturated aqueous solution of ammonium chloride and extracted with diethyl ether. The extract was washed with water and saturated brine, then dried over anhydrous sodium sulfate. The solvent was distilled off to afford 1-acetoxy-2,6-di-tert-butyl-3-methyl-4-propyloxybenzene which was substantially pure on TLC. It was used in the subsequent reaction without further purification.

Workup

  1. stirringthe mixture was stirred for an additional 2 h
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-3c45bbf439dc410589299035dee47ebd
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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