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

HRID 440142Notes

Reaction equation

HRID 440142 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16](O)(=[O:19])[CH:17]=[O:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>ClCCCl>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[O:15][C:17](=[O:18])[CH:16]([OH:19])[C:7]=2[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

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 111,2-DichloroethaneSolvent

Procedure

A mixture of 212.5 g (1.00 mo) of 2,4-di-tert-butylphenol (97%), 163.0 g (1.10 mol) of 50% aqueous glyoxylic acid and 0.5 g (2.6 mmol) of p-toluenesulfonic acid monohydrate in 300 ml of 1,2-dichloroethane is refluxed under nitrogen for 3.5 hours on a water separator. Afterwards the reaction mixture is concentrated on a vacuum rotary evaporator. The residue is taken up in 800 ml of hexane and washed three times with water. The aqueous phases are separated in the separating funnel and further extracted with 300 ml of hexane. The organic phases are combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. The residue yields 262.3 g (~100% ) of analytically pure 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one in the form of a thick yellowish resin (compound (201), Table 2).

Workup

  1. concentrationAfterwards the reaction mixture is concentrated on a vacuum rotary evaporator
  2. washwashed three times with water
  3. customThe aqueous phases are separated in the separating funnel
  4. extractionfurther extracted with 300 ml of hexane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record
ord-ed04dcdf60884573b80fdc340943ae5d
Source dataset
uspto-grants-1996_05
Patent number
US05516920

Reaction notes

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