Benzyl Bromide → 2-(3-(Benzyloxy)phenyl)ethanol

HRID 2389361Notes

Reaction equation

HRID 2389361 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:10][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][OH:1])[CH:9]=[CH:8][CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 834043-Hydroxyphenethyl alcohol

Product 1

HCID 204025442-(3-(Benzyloxy)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(2-hydroxyethyl)phenol (1.0 g) and K2CO3 (1.5 g) in acetone (20 mL) was added (bromomethyl)benzene (1.49 g) at ambient temperature. The reaction mixture was stirred at the same temperature for 17 hours. The resulting mixture was evaporated in vacuo. The residue was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=90:10-70:30) to give 2-[3-(benzyloxy)phenyl]ethanol.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed successively with water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=90:10-70:30)

Sources & evidence

ORD record
ord-3d76e9a5a6e24fa49c6a95691779074c
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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