Benzyl Bromide → 1-Allyl-2-(benzyloxy)4-methoxybenzene

HRID 2115901Notes

Reaction equation

HRID 2115901 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[OH:12])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[O:12][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 64245155-Methoxy-2-allylphenol

Product 1

HCID 689665561-Allyl-2-(benzyloxy)4-methoxybenzeneYield 90.2%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-allyl-5-methoxyphenol (20.30 g, 0.124 mol) in DMF (500 mL) was added potassium carbonate (68.35 g, 0.495 mol) followed by benzyl bromide (23.26 g, 0.136 mol) and tetrabutylammonium iodide (4.57 g, 0.012 mol). The reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with water (1000 mL) to dissolve any solids and extracted with diethyl ether (3×250 mL). The combined organic layers were washed with water (4×500 mL), saturated aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:19) provided 28.44 g (90%) of 1-allyl-2-(benzyloxy)-4-methoxybenzene as a colorless oil. Rf=0.88 (silica, ethyl acetate:hexanes 1:9); Anal. calcd. for C17H18O2: C, 80.28; H, 7.13. Found: C, 82.43; H, 7.09.

Workup

  1. dissolutionto dissolve any solids
  2. extractionextracted with diethyl ether (3×250 mL)
  3. washThe combined organic layers were washed with water (4×500 mL), saturated aqueous sodium chloride (400 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent removed in vacuo
  6. customto give a crude oil
  7. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:19)

Sources & evidence

ORD record
ord-be7ba0bd67294b68b07262a8d1674158
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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