Acetone → Catechol

HRID 1833493Notes

Reaction equation

HRID 1833493 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([CH2:11]C(=O)C)(=[O:10])[CH3:9].[CH3:15][C:16]([CH3:18])=[O:17].C(OO)(=O)C>>[C:1]1([C:6](=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:10])[OH:7].[C:16]1([CH:18]=[CH:11][C:8]([OH:10])=[CH:9][CH:15]=1)[OH:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 996Phenol2×HCID 6585Peracetic Acid2×HCID 31261Acetylacetone

Product 2

HCID 289CatecholHCID 785Hydroquinone

Procedure

A reaction flask having an inner volume of 100 ml and provided with a thermometer, a stirrer, a reflux condenser and a dropping funnel was charged with 32.0 g (0.34 mol) of phenol and 0.0642 g (0.2 percent by weight based on said phenol) of acetyl acetone. To the contents of the flask, 7.6 g (0.034 mol) of an acetone solution of 34.0 percent by weight of peracetic acid was introduced introudced dropwise while under agitation at a temperature of 80° C over a period of 20 minutes. After the termination of said dropwise introduction of peracetic acid, the reaction system was agitated at the same temperature for an additional period of 42 minutes to bring the reaction to completion. Thereafter, the reaction mixture was analyzed for unaltered phenol and formed pyrocatechol and hydroquinone by gas chromatography. The results were 29.10 g, 1.66 g, and 1.09 g respectively. These values indicate the conversion of phenol to be 9.06 percent and the selectivity for dioxy-benzene to be 73.5 percent relative to peracetic acid and 81.2 percent relative to phenol. From the reaction mixture, acetone, formed acetic acid and acetyl acetone were simultaneously recovered by distillation. When the recovered mixture was analyzed for acetyl acetone by means of gas chromatography, the acetyl acetone content was found be 0.0591 g. This value indicates the recovery ratio to be 92 percent.

Workup

  1. customA reaction flask having
  2. customan inner volume of 100 ml and provided with a thermometer, a stirrer, a reflux condenser and a dropping funnel
  3. customthe reaction to completion

Sources & evidence

ORD record
ord-481e162ed8644deca37c11150d998a22
Source dataset
uspto-grants-1978_01
Patent number
US04066707

Reaction notes

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