Catechol → HCID 131726537, compound

HRID 1296730Notes

Reaction equation

HRID 1296730 reaction equation
Cl[Ti:2](Cl)(Cl)Cl.[C:6]1([C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9])[OH:7]>C1(C)C(C)=CC=CC=1>[C:6]1([C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[O-:9])[O-:7].[Ti+4:2].[C:6]1([C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[O-:9])[O-:7]

Participants

4

Reactant 2

HCID 289CatecholHCID 24193Titanium Tetrachloride

Product 1

HCID 131726537HCID 131726537, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of freshly distilled TiCl4 (11 g, 58 mmol) and pyrocatechol (13.7 g, 0.124 mol) was refluxed in 80 mL of xylene during 20 hours. The resulting dark-brown solid was filtered, washed by xylene and dried under vacuum. Titanium catecholate (10.24 g, 66%) was isolated. This salt (2.3 g, 8.7 mmol), pyrocatechol (82.5 g, 0.749 mol), xylene (80 mL) and isobutylene (150 mL) were heated in autoclave during 1.5 hours at 140° C. The solvent was removed and the residue was distilled under vacuum (b.p. −140-145° C., ˜1 mm Hg; m.p. 96-96.5° C.). Yield: 157.4 g (95%). (Also see “Organic Chemistry of Free Radicals”, Moscow, Khimia, 1979, p. 134.)

Workup

  1. filtrationThe resulting dark-brown solid was filtered
  2. washwashed by xylene
  3. customdried under vacuum

Sources & evidence

ORD record
ord-5f671153bcee4ce0bb986fba93249a6c
Source dataset
uspto-grants-2007_07
Patent number
US07247687B2

Reaction notes

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