Benzoate → Benzoic anhydride

HRID 1295545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295545
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8](O)[CH:9]=1)[CH2:5][OH:6].C(O)C1C=CC=CC=1.[C:19]([O-:27])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:5]([O:27][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:6])[C:4]1[CH:7]=[CH:8][CH:9]=[CH:2][CH:3]=1

Komponenten

6

Edukt 3

HCID 242BenzoateHCID 244Benzyl AlcoholHCID 346613,5-Dihydroxybenzyl alcohol

Produkt 1

HCID 7167Benzoic anhydride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

The synthesis of organotelluride catalysts based on 3,5-dihydroxybenzyl alcohol (1) is shown in FIG. 11. 3,5-Bis[3-(tert-butyldimethylsilyloxy)propyl-1-oxy]benzyl alcohol (5) (Francavilla et al., J. Am. Chem. Soc., 123:57 et al. (2001), which is hereby incorporated by reference in its entirety) was converted to the corresponding benzoate 6 in 99% isolated yield with benzoic anhydride and pyridine in the presence of catalytic DMAP. The silyl protecting groups were removed with HF-pyridine to give diol 7 in 89% isolated yield. Diol 7 was converted to the corresponding dibromide 8 in two steps (Wendler et al., Tetrahedron, 3:144 et al. (1958), which is hereby incorporated by reference in its entirety). The mesylate was first prepared, but not isolated, and was then treated in situ with lithium bromide to give dibromide 8 in 87% isolated yield. The addition of PhTeNa to 8 gave 9a with two phenyltelluro groups in 65% isolated yield; 4-Me2NC6H4TeNa, 9b with two dimethylaminophenyltelluro groups in 92% isolated yield; and n-C6H13TeNa, 9c with two hexyltelluro groups in 62% isolated yield.

Aufarbeitung

  1. customisolated

Quellen und Nachweise

ORD-Eintrag
ord-074aa9317faf4ee7890d99266779f1fa
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244295B2

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