Thionyl Chloride → (Phenylthio)acetyl chloride

HRID 582669

Reaktionsgleichung

Reaktionsgleichung von HRID 582669
[S:1]([CH2:8][C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:14]>>[C:2]1([S:1][CH2:8][C:9]([Cl:14])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 59541(Phenylthio)acetic acid

Produkt 1

HCID 4063350(Phenylthio)acetyl chlorideAusbeute 98 %

Versuchsvorschrift

To thiophenoxyacetic acid (8 g, 0.05 mol) was added SOCl2 (8 mL) and the reaction mixture was heated to reflux for 1 h. TLC showed disappearance of the starting material. The excess SOCl2 was removed in vacuo under a fume hood and the product was distilled to afford 8.6 g (98%) of the title compound, bp 85-86° C., 4-5 Torr [lit 117-119° C., 6 Torr (Mooradian, A.; Cavallito, C. J.; Bergman, A. J.; Lawson, E. J.; Suter, C. M. J. Am. Chem. Soc. 1949, 3372)]; 1H NMR (CDCl3) δ 7.48-7.34 (m, 5H), 4.06 (m, 2H); 13C NMR (CDCl3) 169.75, 132.83, 131.44, 129.35, 128.22, 48.48; MS (EI, m/z) 186 (M+)

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe excess SOCl2 was removed in vacuo under a fume hood
  4. distillationthe product was distilled

Quellen und Nachweise

ORD-Eintrag
ord-25bcd47ae52f42ee90d0589c7bd9184c
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925647

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