Methanesulfonic Acid → HCID 19930567, compound

HRID 22573

Reaction equation

HRID 22573 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:15]3[CH:16]=[C:17]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]=3[O:13][C:12]2=[O:28])=[CH:7][CH:6]=1)[CH:2]=C.[CH3:29]S(O)(=O)=O>C(O)(=O)C>[C:24]([C:17]1[CH:18]=[C:19]([C:20]([CH3:22])([CH3:23])[CH3:21])[C:14]2[O:13][C:12](=[O:28])[CH:11]([C:8]3[CH:7]=[CH:6][C:5]4[O:4][CH:1]([CH3:2])[CH2:29][C:10]=4[CH:9]=3)[C:15]=2[CH:16]=1)([CH3:26])([CH3:27])[CH3:25]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 199305653-(4-Allyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one

Product 1

HCID 19930567HCID 19930567, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.80 g (10.0 mmol) of 3-(4-allyloxyphenyl)-5,7-di-tert-butyl-benzofuran-2-one are kept under nitrogen for about 4 hours at 220° C. After cooling, 10 ml of acetic acid and 0.3 ml of methanesulfonic acid are added and the reaction mixture is refluxed for 7 hours. After dilution with 100 ml of water, the product is extracted with dichloromethane. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue on silica gel with the eluant system dichloromethane/hexane=1:2 and crystallisation of the pure fractions from ligroin gives 1.07 g (28%)of 5,7-di-tert-butyl-3-(2-methyl-dihydrobenzofuran-5-yl)benzofuran-2-one, m.p. 136°-152° C. as a mixture of diastereoisomers (compound (101), Table 1).

Workup

  1. temperatureAfter cooling
  2. temperaturethe reaction mixture is refluxed for 7 hours
  3. extractionAfter dilution with 100 ml of water, the product is extracted with dichloromethane
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator
  7. customChromatography of the residue on silica gel with the eluant system dichloromethane/hexane=1:2 and crystallisation of the pure fractions from ligroin

Sources & evidence

ORD record
ord-06cee355fe944f6091fba45c9345e22f
Source dataset
uspto-grants-1995_06
Patent number
US05428177

Linked notes

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