Glyoxylic Acid → HCID 22628567, compound

HRID 278507Notes

Reaction equation

HRID 278507 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]([OH:20])(=O)[CH:17]=[O:18].O.[C:22](OC(=O)C)(=[O:24])[CH3:23]>ClCCCl.COC(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:22]([O:20][CH:16]1[C:7]2[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=2[O:15][C:17]1=[O:18])(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 760Glyoxylic AcidHCID 962WaterHCID 73112,4-Di-tert-butylphenolHCID 7918Acetic Anhydride

Product 1

HCID 22628567HCID 22628567, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 111,2-DichloroethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of 21.2 g (0.10 mol) of 2,4-di-tert-butylphenol (97%), 16.3 g (0.11 mol) of 50% aqueous glyoxylic acid and 0.05 g (0.26 mmol) of p-toluenesulfonic acid monohydrate in 30 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 9.9 ml (0.105 mol) of acetic anhydride and the solution is refluxed for 90 minutes. The reaction mixture is then cooled to room temperature, diluted with 100 ml of tert-butyl methyl ether and washed in succession with water and dilute sodium hydrogencarbonate solution. The aqueous phases are separated and extracted with 50 ml of tert-butyl methyl ether. The organic phases are combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue on silica gel with the solvent system dichloromethane/hexane=2:1 yields 28.0 g (92%) of 3-acetoxy-5,7-di-tert-butyl-3H-benzofuran-2-one (compound (206), Table 2) as a thick reddish resin.

Workup

  1. concentrationAfterwards the reaction mixture is concentrated on a vacuum rotary evaporator
  2. temperaturethe solution is refluxed for 90 minutes
  3. washwashed in succession with water and dilute sodium hydrogencarbonate solution
  4. customThe aqueous phases are separated
  5. extractionextracted with 50 ml of tert-butyl methyl ether
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record
ord-270fe70a318c479590308de71f653c57
Source dataset
uspto-grants-2002_03
Patent number
US06359148B1

Reaction notes

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