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

HRID 989349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989349
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzeneAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-285d2c1cc25847d8971ca966119b6fb8
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638929B2

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