Water → 1-Allyl-2-(benzyloxy)benzene

HRID 1736614Notes

Reaction equation

HRID 1736614 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH:2]=[CH2:3].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[CH2:13]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH:2]=[CH2:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 156242-AllylphenolHCID 24758Sodium hydride

Product 1

HCID 114701341-Allyl-2-(benzyloxy)benzeneYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of 6.71 (50 mmol) of 2-allylphenol in 50 ml of dimethylformamide was added dropwise to a stirred suspension of 2.20 g (55 mol) of a 60% dispersion of sodium hydride in mineral oil in 30 ml of dimethylformamide. The mixture was stirred at 25° C. for 1 hour and then a solution of 5.95 ml (50 mmol) of benzyl bromide in 20 ml of dimethylformamide was added dropwise. After the resulting mixture was stirred at 25° C. for 18 hours 500 ml of water was added and the mixture was extracted with ether. The ether extracts were washed with water and brine, dried (Na2SO4) and concentrated. Chromatography of the residue on a silica gel column, eluting with a 0 to 10% gradient of ethyl acetate in hexane afforded 9.68 g (86.4%) of the product as a colorless liquid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. washThe ether extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. washChromatography of the residue on a silica gel column, eluting with a 0 to 10% gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-2c32e41b66d14afbbfa35224db7187e8
Source dataset
uspto-grants-1996_07
Patent number
US05541286

Reaction notes

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