4-(4-Methoxyphenylsulfanyl)benzoic acid → 4-(4-Methoxyphenylsulfanyl)benzyl alcohol
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=2)=[CH:7][CH:8]=1Komponenten
Versuchsvorschrift
4-(4-Methoxyphenylsulfanyl)benzoic acid was reduced with sodium bis-(methoxyethoxy)-aluminum hydride to provide in 51.5% yield 4-(4-methoxyphenylsulfanyl)benzyl alcohol. Its reaction with thionyl chloride provided in 93.3% yield the corresponding benzyl chloride which treated with sodium cyanide provided in 71.1% 4-(4-methoxyphenylsulfanyl)phenylacetonitrile. Alkaline hydrolysis provided after work-up 47.5% yield of 4-(4-methoxyphenyl-sulfanyl)phenylacetic acid, m.p. 85-87° C. Demethylation of this acid with pyridine hydrochloride provided in 98.0% yield 4-(4-hydroxyphenylsulfanyl) phenylacetic acid, m.p. 83-85° C., which was esterified with methanol in the presence of 4-toluenesulfonic acid to give the required ester as an oil. For C15H14O3S (274.3) calculated: 11.67% S; found: 11.49%. 1H NMR spectrum (CDCl3): H(O) 5.63 bs; CH2 3.58 s; aromatic H on the phenolic nucleus: H(2,6) 6.76 d, J=8.8 Hz; H(3,5) 7.33 d, J=8.8 Hz.
Quellen und Nachweise
- ORD-Eintrag
- ord-1e220d0bf1354b699598ffeb36333498
- Quelldatensatz
- uspto-grants-2001_10
- Patentnummer
- US06303612B1
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