2,4,4-Trimethyl-1-pentene → 2,4,4-Trimethylpent-2-yl dithiobenzoate

HRID 1297485

Reaktionsgleichung

[C:1]([SH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH2:12]>C(Cl)(Cl)(Cl)Cl>[C:1]([S:9][C:11]([CH3:12])([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of dithiobenzoic acid (5 g), 2,4,4-trimethylpentene (7.3 g) and carbon tetrachloride (25 mL) was heated at 70° C. for two days. The resultant mixture was reduced to a crude oil. Purification of the residue, by column chromatography (Kieselgel-60, 70-230 mesh, petroleum spirit 40-60° C. eluent) gave 2,4,4-trimethylpent-2-yl dithiobenzoate (17) (2.74 g, 31.7% yield) as a dark red oil. 1H-nmr (CDCl3) d (ppm): 1.08 (s, 9H, 3×CH3), 1.77 (s, 6H, 2×CH3), 2.26 (s, 2H, CH2), 7.35 (dd, 2H, meta-ArH), 7.49 (dd, 1H, para-ArH) and 7.85 (d, 2H, ortho-ArH). 13C-nmr (CDCl3) d (ppm): 28.3, 31.5, 32.8, 50.5, 57.7, 126.6, 128.1, 131.5 and 147.9. The signal due to C═S (d>220.0 ppm) was beyond the frequency range of the spectrum.

Aufarbeitung

customPurification of the residue

Quellen und Nachweise

ORD-Eintrag: ord-eb974efb442e47dfb88187a713e9b6bd
Quelldatensatz: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07250479B2

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