Methane → Methyl 4-(p-toluene-sulphonyl)-butanoate

HRID 1449405

Reaktionsgleichung

Reaktionsgleichung von HRID 1449405
O[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[C:9]1(C)[C:10]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1.N1C=CC=C[CH:21]=1.C>C(OCC)C>[C:13]1([CH3:21])[CH:14]=[CH:9][C:10]([S:15]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])(=[O:16])=[O:17])=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 297MethaneHCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 70217Butanoic acid, 4-hydroxy-, methyl ester

Produkt 1

HCID 21671020Methyl 4-(p-toluene-sulphonyl)-butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

25 g. Methyl 4-hydroxybutanoate were mixed with 47.5 g. toluene-sulphonyl chloride and 250 ml. dry pyridine at 5° C. and kept at this temperature for 17 hours, whereafter the reaction mixture was poured into 2 liters ice water. The oil thus formed was extracted with diethyl ether and the ethereal extract was washed with 500 ml. 6 N hydrochloric acid to remove excess pyridine, followed by washing with a saturated aqueous solution of sodium bicarbonate until neutral. Concentration of the organic layer gave 32.5 g. of a yellow oil which was dissolved in diethyl ether, treated with decolorising charcoal, filtered and the filtrate concentrated to give 30.5 g. of a pale yellow oil which slowly crystallised at 5° C. Thin layer chromatography (petroleum ether/dichloromethane/acetone 6:3:1 v/v/v) showed the product to be pure. The methyl 4-(p-toluene-sulphonyl)-butanoate thus obtained had a melting point of 23° C.

Aufarbeitung

  1. customThe oil thus formed
  2. extractionwas extracted with diethyl ether
  3. extractionthe ethereal extract
  4. washwas washed with 500 ml
  5. custom6 N hydrochloric acid to remove excess pyridine
  6. washby washing with a saturated aqueous solution of sodium bicarbonate until neutral
  7. customConcentration of the organic layer gave 32.5 g
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated
  10. customto give 30.5 g
  11. customof a pale yellow oil which slowly crystallised at 5° C

Quellen und Nachweise

ORD-Eintrag
ord-43e47ce38b9b4f3dab56503e4447474c
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04190671

Verknüpfte Notizen

Wird geladen…