Benzyl Bromide → 3-Benzoxymethylcyclohexene

HRID 54016Notes

Reaction equation

HRID 54016 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([CH2:13][OH:14])[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8]1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH4+].[Cl-]>C1COCC1>[CH2:13]([O:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 155123-Cyclohexene-1-methanolHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 157413843-BenzoxymethylcyclohexeneYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium t-butoxide (1.0M in THF, 8.27 mL, 8.27 mmol) was added dropwise to a solution of (±)-3 cyclohexene-1-methanol (853 mg, 7.60 mmol) in THF (35 mL) at 25° C. under N2. The resultant mixture was stirred at 25° C. for 30 minutes. Benzyl bromide (1.0 mL, 8.37 mmol) was added dropwise. The reaction mixture was allowed to stir at room temperature for 16 hours and then treated with saturated aqueous NH4Cl (5 mL) and concentrated. The residue was dissolved in ether (50 mL), washed with water (20 mL) and brine (20 mL), and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was subjected to radial chromatography on silica gel eluting with 5 percent EtOAc in hexane to give (±)-3-(benzyloxy)methyl-1-cyclohexene (1.42 g, 92 percent) as a colorless oil. NMR

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ether (50 mL)
  3. washwashed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-349f6d5621f04325b07bc23a4fef851f
Source dataset
uspto-grants-1997_04
Patent number
US05621098

Reaction notes

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