Benzyl Bromide → (((2-Methylprop-2-en-1-yl)oxy)methyl)benzene

HRID 654983Notes

Reaction equation

HRID 654983 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4](=[CH2:6])[CH3:5].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1.C(OCC)(=O)C>[CH2:8]([O:7][CH2:3][C:4]([CH3:6])=[CH2:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10557Methallyl alcoholHCID 24758Sodium hydride

Product 1

HCID 250510(((2-Methylprop-2-en-1-yl)oxy)methyl)benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen stream, 50 % sodium hydride (5.28 g; 0.11 mole) was added to dry tetrahydrofuran (50 ml), and a solution of methallyl alcohol (7.2 g;0.1 mole) in dry tetrahydrofuran (20 ml) was portionwise added thereto with ice-cooling, followed by stirring for 30 minutes. A solution of benzyl bromide (17.1 g; 0.1 mole) in dry tetrahydrofuran (20 ml) was added thereto to quench the reaction. The reaction mixture was diluted with ethyl acetate and washed successively with lN hydrochloric acid, water and an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure gave 1-benzyloxy-2-methyl-2-propene.

Workup

  1. temperaturewith ice-cooling
  2. customto quench
  3. customthe reaction
  4. washwashed successively with lN hydrochloric acid, water
  5. dry with materialan aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b23d4f1b4267449582f20fe4153394d7
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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