Hydrochloric Acid → 4-(2-Naphthylsulphonyl)benzoic acid

HRID 427435

Reaktionsgleichung

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[Mn]([O-])(=O)(=O)=[O:23].[K+].Cl.C(OCC)(=O)C>O.[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:14]1[CH:21]=[CH:20][C:17]([C:18]([OH:23])=[O:19])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

4-(Naphthalene-2-sulphonyl)benzaldehyde (0.97 g) was suspended in water (25 ml) containing cetyltrimethylammonium bromide (58 mg). The mixture was stirred and heated to 60° C., and potassium permanganate (0.95 g) was added in small portions over 1 hour. Heating was continued for a further 2 hours. The mixture was cooled to room temperature and was acidified with 2M hydrochloric acid. Ethyl acetate was added to the stirred mixture, which was filtered through a pad of celite. The ethyl acetate layer was washed with brine, dried (MgSO4), and evaporated to afford 4-(naphthalene-2-sulphonyl)benzoic acid (0.42 g) as solid residue; NMR: 7.7(dd,1H); 7.95(dd,1H), 8.1-8.2(m,8H); 8.7(d,1H); microanalysis, found; C,58.6; H,3.9%; C17H12O4S.2H2O requires: C,58.6; H,4.6%; MS: m/z 312(M H)+.

Aufarbeitung

temperatureHeating
temperatureThe mixture was cooled to room temperature
filtrationwas filtered through a pad of celite
washThe ethyl acetate layer was washed with brine
dry with materialdried (MgSO4)
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-7f0f6e2c1ab046e9bf1dba34cb4817e0
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06313127B1

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