Glyoxylic Acid → 7-tert-butyl-3-hydroxy-5-methyl-3H-benzofuran-2-one

HRID 1938829Notes

Reaction equation

HRID 1938829 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].[C:13](O)(=[O:16])[CH:14]=[O:15].O>ClCCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:5]1[C:6]2[O:12][C:14](=[O:15])[CH:13]([OH:16])[C:7]=2[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 760Glyoxylic AcidHCID 962WaterHCID 170042-tert-Butyl-4-methylphenol

Product 1

HCID 186202687-tert-butyl-3-hydroxy-5-methyl-3H-benzofuran-2-oneYield 82%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 49.8 g (0.30 mol) of 2-tert-butyl-4-methylphenol, 48.9 g (0.33 mol) of 50% aqueous glyoxylic acid and 0.15 g (0.79 retool) of p-toluenesulfonic acid monohydrate in 90 ml of 1,2-dichloroethane is refluxed under nitrogen for 3.5 hours on a water separator. The reaction mixture is afterwards cooled to +5° C and the precipitate is isolated by filtration and washed with cold 1,2-dichloroethane. The filter residue is dried under a high vacuum at room temperature, affording 54.0 g (82%) of 7-tert-butyl-3-hydroxy-5-methyl-3H-benzofuran-2-one, m.p. 152-160° C (compound (102), Table 1).

Workup

  1. temperatureThe reaction mixture is afterwards cooled to +5° C
  2. customthe precipitate is isolated by filtration
  3. washwashed with cold 1,2-dichloroethane
  4. customThe filter residue is dried under a high vacuum at room temperature

Sources & evidence

ORD record
ord-1d6ad31ea6c7410995f508d577de6fc1
Source dataset
uspto-grants-1997_12
Patent number
US05693829

Reaction notes

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