Water → Hexahydroxytriphenylene

HRID 1289336Notes

Reaction equation

HRID 1289336 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:8]([O:33]C)=[C:9]2[C:22](=[CH:23][CH:24]=1)[C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:15]1[C:14]([O:25]C)=[C:13]([O:27]C)[C:12]([O:29]C)=[C:11]([O:31]C)[C:10]2=1.O>ClCCl>[OH:6][C:7]1[C:8]([OH:33])=[C:9]2[C:22](=[CH:23][CH:24]=1)[C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:15]1[C:14]([OH:25])=[C:13]([OH:27])[C:12]([OH:29])=[C:11]([OH:31])[C:10]2=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22481127Hexamethoxytriphenylene

Product 1

HCID 18430414Hexahydroxytriphenylene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (8.6 g, 0.034 mol) in dry dichloromethane (80 ml) was added to hexamethoxytriphenylene (2 g, 0.0049 mol) in dry dichloromethane (100 ml) under a dry nitrogen atmosphere at -80° C. The mixture was allowed to warm to room temperature overnight. Water was added and the dichloromethane was removed under reduced pressure. The crude product was filtered off. The hexahydroxytriphenylene was purified by recrystallisation from water.

Workup

  1. customthe dichloromethane was removed under reduced pressure
  2. filtrationThe crude product was filtered off
  3. customThe hexahydroxytriphenylene was purified by recrystallisation from water

Sources & evidence

ORD record
ord-e59bea2704b5436d95f04a6e31feb1dc
Source dataset
uspto-grants-1998_05
Patent number
US05750050

Reaction notes

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