Guaiacol → 2-(2-Bromoethoxy)anisole

HRID 1059127Notes

Reaction equation

HRID 1059127 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[CH2:10](Br)[CH2:11][Br:12].[OH-].[Na+]>>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][CH2:10][CH2:11][Br:12]

Participants

4

Reactant 3

HCID 460GuaiacolHCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide

Product 1

HCID 17990992-(2-Bromoethoxy)anisole

Procedure

0.2 mole(22.4 ml) of guaiacol and 0.4 mole (34.6 ml) of ethylene dibromide are heated to 100° C. while stirring vigorously, and within 30 minutes, 125 ml of 1.6 N sodium hydroxide solution is added to continue the stirring and the pH value is adjusted to 7. Upon cooling, the mixed solution's organic layer is extracted with chloroform and rinsed with 2N sodium hydroxide before rising again with saturated sodium chloride solution and magnesium sulfate. Upon reduction, the solution is filled into the silicone tube for separation. Using the ratio of hexane: ethyl acetate=9:1 as the diluent, white crystallized product, 2-(2-methoxyphenoxy ethylbromide, is obtained.

Workup

  1. temperatureUpon cooling
  2. extractionthe mixed solution's organic layer is extracted with chloroform
  3. washrinsed with 2N sodium hydroxide
  4. additionUpon reduction, the solution is filled into the silicone tube for separation

Sources & evidence

ORD record
ord-7ba73f8b22b14657b2b0ee332550c074
Source dataset
uspto-grants-2003_02
Patent number
US06518450B2

Reaction notes

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