4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl ester

HRID 18669

Reaktionsgleichung

Reaktionsgleichung von HRID 18669
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12])([CH3:3])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[O:12][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 183649974-Methoxy-2-(propan-2-yl)phenol

Produkt 1

HCID 44248852Toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl esterAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a solution of 180 g of 2-Isopropyl-4-methoxy-phenol (1.084 moles) in 2.5 L toluene was added 206.7 g p-toluene sulfonylchloride (1.084 moles), and the reaction mixture was stirred vigorously The resultant mixture was cooled to 10° C., and triethylamine (3 mol) was gradually added, keeping the temperature below 50 degrees C. The reaction mixture was aged for 3 hours at approximately 50° C. and then allowed to cool to RT. An HPLC sample obtained at this point showed completion of the reaction. The resultant suspension was filtered and the filter-cake was washed with 300 mL toluene. The collected filtrate was distilled under vacuum until the pot-temperature reached 65° C., and 1 L of methanol was added to the mixture. The methanolic solution was stirred for 30 minutes at reflux; then the mixture was permitted to cool overnight. The white crystalline solid which separated was collected by filtration and dried at 50° C. under vacuum to yield a total of 332 grams of toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl ester, representing an yield of 95.7%:m.p. 85.1 degrees C.

Aufarbeitung

  1. customthe temperature below 50 degrees C
  2. temperatureto cool to RT
  3. customAn HPLC sample obtained at this point
  4. customcompletion of the reaction
  5. filtrationThe resultant suspension was filtered
  6. washthe filter-cake was washed with 300 mL toluene
  7. distillationThe collected filtrate was distilled under vacuum until the
  8. custompot-temperature reached 65° C.
  9. addition1 L of methanol was added to the mixture
  10. temperatureat reflux
  11. temperatureto cool overnight
  12. customThe white crystalline solid which separated
  13. filtrationwas collected by filtration
  14. customdried at 50° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6486c783183b420d8171de8ada6fee30
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741484B2

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