3-Hydroxybenzyl alcohol → [3-(2-Methoxyethoxy)phenyl]methanol

HRID 45228

Reaction equation

HRID 45228 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:16][O:17][CH2:18][CH2:19]Br>CC#N>[CH3:16][O:17][CH2:18][CH2:19][O:9][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 20110194[3-(2-Methoxyethoxy)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10 g (80.6 mmol) of 3-(hydroxymethyl)phenol, 78.4 g (241.7 mmol) of Cs2CO3 and 8.4 mL (88.6 mmol) of bromoethyl methyl ether in 150 mL of CH3CN is heated for 12 hours at 110° C. After cooling to room temperature, the medium is filtered, concentrated under reduced pressure, taken up in 500 mL of DCM, washed with brine (2×100 mL) dried over Na2SO4, filtered and then concentrated under reduced pressure. 10.9 g of 3-(2-methoxyethoxy)phenyl]methanol are obtained in the form of a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe medium is filtered
  3. concentrationconcentrated under reduced pressure
  4. washwashed with brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custom10.9 g of 3-(2-methoxyethoxy)phenyl]methanol are obtained in the form of a yellow oil

Sources & evidence

ORD record
ord-508484e1afec43eb83cbb806dec4e237
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Linked notes

Loading…