Benzyl Bromide → 2-(Benzyloxy)-1-ethyl-4-methoxybenzene

HRID 392868Notes

Reaction equation

HRID 392868 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 125297512-Ethyl-5-methoxyphenol

Product 1

HCID 226620992-(Benzyloxy)-1-ethyl-4-methoxybenzeneYield 102%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under a nitrogen atmosphere, 18.30 g (120.2 mmol) of 2-ethyl-5-methoxyphenol (2) was dissolved in 150 ml of acetone. To this solution was added 33.24 g (240.5 mmol) of potassium carbonate followed by 15.02 ml (126.3 mmol) of benzyl bromide. The resultant mixture was heated to reflux for 16 hours. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate (300 ml) and water (300 ml). The ethyl acetate layer was separated, washed with 1M NaOH (2×200 mL) and brine (1×200 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield 29.70 g of crude 3-benzyloxy-4-ethyl-1-methoxybenzene (3). Chromatography of the crude product on 400 g of silica gel 60 (EM Science) using 97:3 hexane: ethyl acetate yielded 12.62 g (43%) of 3-benzyloxy-4-ethyl-1-methoxybenzene (3).

Workup

  1. temperatureto reflux for 16 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate (300 ml) and water (300 ml)
  4. customThe ethyl acetate layer was separated
  5. washwashed with 1M NaOH (2×200 mL) and brine (1×200 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df4784007749475cab113dbbc70b99f9
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

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