Water → 3-(Phenylmethoxy)benzenepropanol

HRID 2389360Notes

Reaction equation

HRID 2389360 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CC#N>[CH2:18]([O:11][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:10]=[CH:9][CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 103518713-Hydroxybenzenepropanol

Product 1

HCID 126481553-(Phenylmethoxy)benzenepropanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(3-hydroxypropyl)phenol (1.27 g) in MeCN (12.7 mL) were added K2CO3 (1.73 g) and benzyl bromide (1.05 mL) at ambient temperature and the mixture was stirred at 60° C. for 16 hours. Water (15 mL) was added to the mixture at ambient temperature and the resulting mixture was extracted with EtOAc (20 mL, two times). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=3:1) to afford 3-[3-(benzyloxy)phenyl]-1-propanol (1.77 g) as a colorless oil.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (20 mL, two times)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-eb40e38cdcdb4b7393cbdafcf02bb6ba
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…