Dichloromethane → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 78704

Reaktionsgleichung

Reaktionsgleichung von HRID 78704
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(Cl)Cl>O.C1COCC1>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH3:3])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8178Triethylene glycol monomethyl etherHCID 14798Sodium Hydroxide

Produkt 1

HCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of NaOH (1.69 g, 42.2 mmol) in H2O (11 mL) was added a solution of triethylene glycol monomethyl ether (5.00 mL, 31.9 mmol) in THF (11 mL) under nitrogen, while the temperature was maintained below 5° C. by cooling with an ice-salt bath. At the same temperature, a solution of p-toluenesulfonyl chloride (6.08 g, 31.9 mmol) in THF (13 mL) was added dropwise over 1 h. The reaction mixture was poured into water and DCM was added. The layers were separated, and the aqueous layer was extracted with DCM (three times). The combined organic layers were washed with water (twice) and brine (twice), dried over anhydrous MgSO4, filtered off and evaporated to dryness to give 16 (8.43 g, 83%): 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=8.3 Hz, 2H), 7.30 (d, J=8.2 Hz, 2H), 4.16 (t, 2H), 3.50-3.70 (m, 10H), 3.32 (s, 3H), 2.40 (s, 3H).

Aufarbeitung

  1. temperaturewhile the temperature was maintained below 5° C.
  2. temperatureby cooling with an ice-salt bath
  3. additionwas added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (three times)
  6. washThe combined organic layers were washed with water (twice) and brine (twice),
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered off
  9. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fccf92e18e414a3081ce368e79631bfb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841460B2

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