Water → 2-(3-(2,2-Diethoxyethoxy)phenyl)ethanol

HRID 1689250Notes

Reaction equation

HRID 1689250 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.Br[CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].O>CN(C=O)C>[CH2:21]([O:20][CH:19]([O:23][CH2:24][CH3:25])[CH2:18][O:16][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][OH:7])[CH:15]=[CH:14][CH:13]=1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 834043-Hydroxyphenethyl alcohol

Product 1

HCID 579890052-(3-(2,2-Diethoxyethoxy)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Caesium carbonate (8.84 g) was added to a solution of 3-(2-hydroxyethyl)phenol (2.5 g) and 2-bromo-1,1-diethoxyethane (3.74 g) in DMF (50 mL), and the resulting mixture was stirred at 90° C. overnight, then allowed to cool. The mixture was poured into water and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, then dried over anhydrous sodium sulphate and purified by flash chromatography on silica eluted with a gradient of diethyl ether in isohexane to afford the subtitled compound as a pale yellow oil. Yield 3.0 g.

Workup

  1. temperatureto cool
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. custompurified by flash chromatography on silica
  6. washeluted with a gradient of diethyl ether in isohexane

Sources & evidence

ORD record
ord-d5e8c5d1e88c41c89839e579e865d2e5
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…