Benzyl Bromide → 3-(Benzyloxy)-5-methylphenol

HRID 1822282Notes

Reaction equation

HRID 1822282 reaction equation
[C:1]1([OH:9])[CH:8]=[C:6]([CH3:7])[CH:5]=[C:3]([OH:4])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:4][C:3]1[CH:2]=[C:1]([OH:9])[CH:8]=[C:6]([CH3:7])[CH:5]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10436OrcinolHCID 11430Potassium Carbonate

Product 1

HCID 109983793-(Benzyloxy)-5-methylphenolYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. mixture of orcinol (10.0 g, 80.6 mmol) and 325 mesh potassium carbonate (12.25 g, 88.6 mmol) in DMF (100 mL) is treated dropwise with benzyl bromide (6.91 g, 40.4 mmol). The mixture was then warmed to rt and stirred for 20 hours under N2. The reaction is filtered, and the filtrate is acidified with 1 N HCl. The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 5/1 hexanes/ethyl acetate to afford 4.88 g (57%) of the title compound. Rf=0.40 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C14H14O2 214, found 215 (M+1, 100%).

Workup

  1. filtrationThe reaction is filtered
  2. additionThe mixture is then diluted with Et2O
  3. extractionextracted with water
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customthe solvent is removed in vacuo
  6. customto afford crude product that
  7. customis absorbed on silica gel
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-fd60e69a92ae4effbc736376342e4d1c
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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