4-Toluenesulfonyl chloride → p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester

HRID 2165158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165158
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH:20]([CH2:24][OH:25])[CH2:21]2)=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH:20]([CH2:24][O:25][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH2:21]2)=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 10797825(7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

Produkt 1

HCID 11210176p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

20.96 g (110 mmol) of p-toluenesulphonic acid chloride are added at room temperature, while stirring, to a solution of 19.2 g (100 mmol) of 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-methanol in 80 ml of absolute pyridine, the slightly exothermic reaction being maintained at room temperature with an ice bath. The reaction mixture is stirred at room temperature for 1 hour to complete the reaction and is then diluted with ice-water and extracted with diethyl ether. The organic phase is washed while ice-cold with 2N hydrochloric acid and water, is dried over sodium sulphate, filtered and concentrated by evaporation under reduced pressure. The resulting oil is crystallised from diethyl ether/pentane to yield p-toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester of m.p. 64°-66°.

Aufarbeitung

  1. customthe slightly exothermic reaction
  2. customthe reaction
  3. extractionextracted with diethyl ether
  4. washThe organic phase is washed while ice-cold with 2N hydrochloric acid and water
  5. dry with materialis dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe resulting oil is crystallised from diethyl ether/pentane

Quellen und Nachweise

ORD-Eintrag
ord-6ed8d34030984aa5aca4d36f36fd4b74
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939160

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