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

HRID 2213794Notes

Reaction equation

HRID 2213794 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].S(C1C=CC(C)=CC=1)(OC[CH2:15][Cl:16])(=O)=O.[C:24](=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:16][CH2:15][CH2:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][CH3:24]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium Carbonate

Product 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzeneYield 52.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 52.88 g (0.426 mole) of guaiacol, 100 g (0.426 mole) of chloroethyl tosylate, 88.3 g (0.639 mole) of powdered potassium carbonate and 600 mL of 2-butanone is stirred mechanically and refluxed for 2 days. The reaction is filtered and the solid is rinsed with 2-butanone. The filtrate is evaporated and the residue taken up in ether and washed with 1N NaOH to remove unreacted guaiacol. The ether layer is dried over sodium sulfate, filtered and evaporated to give an oil which slowly crystallized. The solid is isolated with cold cyclohexane to give 41.47 g (52%) of 1-(2-Chloroethoxy)-2-methoxybenzene as a white solid, m.p. 42–3° C.

Workup

  1. temperaturerefluxed for 2 days
  2. filtrationThe reaction is filtered
  3. washthe solid is rinsed with 2-butanone
  4. customThe filtrate is evaporated
  5. washwashed with 1N NaOH
  6. customto remove unreacted guaiacol
  7. dry with materialThe ether layer is dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give an oil which
  11. customslowly crystallized
  12. customThe solid is isolated with cold cyclohexane

Sources & evidence

ORD record
ord-457dd9b08e414a71bf0215fe6cbd9fa8
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

Loading…