1-Bromo-2-methylpropane → HCID 13518475, compound

HRID 1906715Notes

Reaction equation

HRID 1906715 reaction equation
[CH2:1](Br)[CH:2]([CH3:4])[CH3:3].[Mg].[CH2:7]([Cl:16])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]>[Na]>[CH3:3][CH:2]([CH2:1][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH2:7][Cl:16])[CH3:4]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 107572-ChloroacetophenoneHCID 5462224Magnesium

Product 1

HCID 13518475HCID 13518475, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent2×

Procedure

The Grignard reagent generated from isobutyl bromide (0.1 mol, 13.7 g) in sodium dry diethyl ether (50 ml) and magnesium turnings (0.11 g atoms; 2.6 g) was added dropwise to a solution of phenacyl chloride (0.05 mol, 7.7 g) in sodium dry diethyl ether (100 ml) so that gentle reflux was maintained. The solution was then stirred at room temperature for 1 hour and the magnesium complex destroyed by pouring into a saturated ammonium chloride solution (200 ml). The ethereal extract was washed with water (3×150 ml) and dried (Na2SO4). Removal of the solvent gave a colourless liquid which distilled at reduced pressure to give 2-methyl-4-phenyl-5-chloro-pentan-4-ol (70%), b.p. 86°-88°/0.01 mm Hg.

Workup

  1. temperaturethat gentle reflux
  2. temperaturewas maintained
  3. customthe magnesium complex destroyed
  4. additionby pouring into a saturated ammonium chloride solution (200 ml)
  5. extractionThe ethereal extract
  6. washwas washed with water (3×150 ml)
  7. dry with materialdried (Na2SO4)
  8. customRemoval of the solvent
  9. customgave a colourless liquid which
  10. distillationdistilled at reduced pressure

Sources & evidence

ORD record
ord-cc985cbf84084deda6b39d2fef56d01f
Source dataset
uspto-grants-1987_03
Patent number
US04654332

Reaction notes

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