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

HRID 1593203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593203
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].Br[CH2:11][CH2:12][Cl:13].[OH-].[Na+]>>[Cl:13][CH2:12][CH2:11][O:3][C:2]1[C:1]([O:8][CH3:9])=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 3

HCID 460GuaiacolHCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium Hydroxide

Produkt 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzeneAusbeute 96,4 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Guaiacol (6.2 g, 50 mmol) and 1-bromo-2-chloro-ethane (8.4 mL, 100 mmol) were mixed thoroughly and heated at 100° C. for 30 minutes. Then, 31 ml of 1.6 N NaOH aqueous solution was added into the mixture to bring the pH to about 7.0. After cooling, the mixture was extracted with chloroform. The chloroform layer was partitioned with 20% NaOH aqueous solution, water and saturated NaCl aqueous solution in sequence. The organic portion was dried with anhydrous sodium sulfite and evaporated to dryness to obtain O-(2-chloroethyl)guaiacol (18) (9 g; yield 96%). Rf 0.67 (chloroform with saturated ammonia water); IR (KBr) νmax 2934 (m), 1593 (s), 1504 (s), 1455 (s), 1254 (s), 1224 (s), 1178 (s), 1125 (s), 1028 (m) cm−1; 1H NMR (CDCl3, 400MHz): δ 6.94 (4H, m), 4.26 (2H, t, J=6.3Hz), 3.85 (3H, s, 2-OMe), 3.81 (2H, t, J=6.3Hz).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with chloroform
  3. customThe chloroform layer was partitioned with 20% NaOH aqueous solution, water and saturated NaCl aqueous solution in sequence
  4. dry with materialThe organic portion was dried with anhydrous sodium sulfite
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ec80f41007de43fdb1fdbbf61c11d120
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294715B2

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