Benzoate → Benzoic anhydride

HRID 1295546Notes

Reaction equation

HRID 1295546 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O-:17])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:1]([O:17][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 242BenzoateHCID 244Benzyl Alcohol

Product 1

HCID 7167Benzoic anhydride

Procedure

The synthesis of tetratelluride catalysts based on dendritic wedge 3 is shown in FIG. 15. Benzyl alcohol 16 (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 benzoate 17 in 93% isolated yield with benzoic anhydride as previously described. The four silyl groups were removed with HF-pyridine to give tetraol 18 in 88% isolated yield. As before, the hydroxyl groups were converted via the mesylate to the corresponding bromides (Wendler et al., Tetrahedron, 3:144 et al. (1958), which is hereby incorporated by reference in its entirety) to give tetrabromide 19 in 52% overall yield. The addition of excess PhTeNa to 19 gave tetratelluride 20a in 65% isolated yield; 4-Me2NC6H4TeNa, tetratelluride 20b in 92% isolated yield; and n-C6H13TeNa, tetratelluride 20c in 51% isolated yield.

Workup

  1. customThe synthesis of tetratelluride catalysts
  2. customisolated

Sources & evidence

ORD record
ord-6132630da6c843e0985918450d57d301
Source dataset
uspto-grants-2007_07
Patent number
US07244295B2

Reaction notes

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