2,4-Di-tert-butylphenol → HCID 9951074, compound

HRID 2380388Notes

Reaction equation

HRID 2380388 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].[CH2:16]([O:18][C:19]1[CH:29]=[CH:28][C:22]([CH:23](O)[C:24](O)=[O:25])=[CH:21][CH:20]=1)[CH3:17]>>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[O:15][C:24](=[O:25])[CH:23]([C:22]3[CH:28]=[CH:29][C:19]([O:18][CH2:16][CH3:17])=[CH:20][CH:21]=3)[C:7]=2[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 73112,4-Di-tert-butylphenolHCID 18955528HCID 18955528, compound

Product 1

HCID 9951074HCID 9951074, compoundYield 92.1%

Procedure

A mixture of 309 g (1.50 mol) of 2,4-di-tert-butylphenol and 196.2 g (1.0 mol) of 4-ethoxymandelic acid is stirred at 140°-150° C. for 2 hours under a nitrogen atmosphere. Stirring at 150° C. is then continued for 1.5 hours under a slight vacuum (50 mbar). Excess 2,4-di-tert-butylphenol is distilled off in a high vacuum. Crystallisation of the residue from 150 ml of xylene and 250 ml of ethanol gives 337.7 g (92%) of 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, melting point 132°-134° C. (compound (101), Table 1).

Workup

  1. stirringStirring at 150° C.
  2. waitis then continued for 1.5 hours under a slight vacuum (50 mbar)
  3. distillationExcess 2,4-di-tert-butylphenol is distilled off in a high vacuum
  4. customCrystallisation of the residue from 150 ml of xylene and 250 ml of ethanol

Sources & evidence

ORD record
ord-065d3c07188849c0a5d4633479fd0d39
Source dataset
uspto-grants-1994_11
Patent number
US05367008

Reaction notes

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