Catechol → 3,6-di-tert-butyl-catechol

HRID 1296731Notes

Reaction equation

HRID 1296731 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][C:10](=[CH2:12])[CH3:11]>C1(C)C(C)=CC=CC=1>[C:10]([C:5]1[CH:6]=[CH:7][C:8]([C:10]([CH3:12])([CH3:11])[CH3:9])=[C:1]([OH:2])[C:3]=1[OH:4])([CH3:11])([CH3:9])[CH3:12]

Participants

4

Reactant 2

HCID 289CatecholHCID 8255Isobutylene

Product 1

HCID 37121923,6-di-tert-butyl-catechol

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. customThe solvent was removed
  2. distillationthe residue was distilled under vacuum (b.p. −140-145° C., ˜1 mm Hg; m.p. 96-96.5° C.)

Sources & evidence

ORD record
ord-32f7b01476244453ab0d2f43e6288ff9
Source dataset
uspto-grants-2007_07
Patent number
US07247687B2

Reaction notes

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