Guaiacol → 1-(2-Chloroethoxy)-2-methoxybenzene

HRID 397613

Reaction equation

HRID 397613 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].Br[CH:11]([Cl:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:13][CH2:11][CH2:12][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 116541-Bromo-1-chloroethane

Product 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzeneYield 35%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 2-methoxyphenol (14.4 g, 116 mmol) in 2-butanone (200 mL) was added bromochloroethane (69.0 g, 480 mmol) followed by the addition of potassium carbonate (40.0 g, 280 mmol). The reaction mixture was mechanically stirred and heated to reflux for 24 h, then cooled to room temperature. The solids were filtered off and the solvent was removed under vacuum. The residue was dissolved in diethyl ether and washed with 10% of NaOH, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by silica gel column chromatography (25% EtOAc/hexane) afforded 7.55 g (35%) of a solid: mp 36-38°C. (Lit.2 41-43° C,); 1H NMR (DMSO, 400 MHz), 3.75 (s, 3H), 3.91 (dd, 2H), 4.20 (dd, 2H), 6.86-6.99 (m, 4H); MS (EI) m/z 186 (M+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. filtrationThe solids were filtered off
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in diethyl ether
  6. washwashed with 10% of NaOH
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel column chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-027af8e544894d078dc39fff3fbae2cd
Source dataset
uspto-grants-2003_08
Patent number
US06610712B2

Linked notes

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