Glyoxylic Acid → 5,7-Di-tert-butyl-3-hydroxy-2-benzofuranone

HRID 985733Notes

Reaction equation

HRID 985733 reaction equation
O.[C:2]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[OH:16])([CH3:5])([CH3:4])[CH3:3].[C:17](O)(=[O:20])[CH:18]=[O:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:12]([C:10]1[CH:11]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[C:7]2[O:16][C:18](=[O:19])[CH:17]([OH:20])[C:8]=2[CH:9]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 760Glyoxylic AcidHCID 962WaterHCID 73112,4-Di-tert-butylphenolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 68508215,7-Di-tert-butyl-3-hydroxy-2-benzofuranone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 15 l multi-necked vessel with stirrer, dropping funnel, water separator, condenser and thermometer is charged with stirring and in succession with 300 ml of toluene, 212 g of 97% 2,4-di-tert-butylphenol (Aldrich 99%), 121.9 ml of 50% strength aqueous glyoxylic acid and 0.5 g of p-toluenesulfonic acid monohydrate. The reaction mixture is subsequently refluxed vigorously with thorough stirring. This is accompanied by the separation of the water present in the glyoxylic acid, and the water of reaction from the first stage. After a reflux time of about 3 h, the separation of water ends, to leave a homogeneous, pale yellow solution of 5,7-di-t-butyl-3-hydroxybenzofuran-2-one. Thereafter, the toluene is distilled off under atmospheric pressure and with a heating-bath temperature of up to 142° C. The crystalline solid is subsequently dried at 80° C./50 mbar.

Workup

  1. customA 15 l multi-necked vessel with stirrer, dropping
  2. temperatureThe reaction mixture is subsequently refluxed vigorously with thorough stirring
  3. customThis is accompanied by the separation of the water present in the glyoxylic acid
  4. customthe water of reaction from the first stage
  5. customAfter a reflux time of about 3 h, the separation of water

Sources & evidence

ORD record
ord-cba6545d981640948905f42eee63bf5b
Source dataset
uspto-grants-2005_03
Patent number
US06872839B1

Reaction notes

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