2,4-Di-tert-butylphenol → 3-(4-Hydroxy-3,5-dimethylphenyl)-5,7-bis(2-methyl-2-propanyl)-1-benzofuran-2(3H)-one

HRID 375992Notes

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].[CH3:16][C:17]1[CH:18]=[C:19]([CH:25]=[C:26]([CH3:29])[C:27]=1[OH:28])[CH:20](O)[C:21](O)=[O:22]>C(O)(=O)C.CS(O)(=O)=O>[CH3:16][C:17]1[CH:18]=[C:19]([CH:20]2[C:7]3[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]=3[O:15][C:21]2=[O:22])[CH:25]=[C:26]([CH3:29])[C:27]=1[OH:28]

Participants

Conditions

Temperature: 95 °C

Procedure

1.5 ml (23 mmol) of methanesulfonic acid are added to a mixture of 154.8 g (0.75 mol) of 2,4-di-tert-butylphenol and 98.1 g (0.50 mol) of 3,5-dimethyl-4-hydroxymandelic acid in 500 ml of acetic acid which is stirred at 95° C. under nitrogen. After about 4 minutes, crystallisation of the product in the form of fine, white crystals begins. The reaction mixture is refluxed for another hour, then cooled to about 15° C., and the precipitated product is filtered off. The residue is washed with 250 ml of acetic acid and with 1500 ml of water. Drying gives 161.5 g (88%) of 3-(3,5-dimethyl-4-hydroxyphenyl)-5,7-di-tert-butylbenzofuran-2-one, melting point 225°-228° C. (compound (107), Table 1).

Workup

customcrystallisation of the product in the form of fine, white crystals
temperatureThe reaction mixture is refluxed for another hour
temperaturecooled to about 15° C.
filtrationthe precipitated product is filtered off
washThe residue is washed with 250 ml of acetic acid and with 1500 ml of water
customDrying

Sources & evidence

ORD record: ord-f31e38393c7c4eef8e7a85a8581f1cae
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488117

Reaction notes

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