Methanesulfonic Acid → HCID 18961267, compound

HRID 1708261Notes

Reaction equation

HRID 1708261 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]([CH2:19][O:20][C:21]1[CH:31]=[CH:30][C:24]([CH:25](O)[C:26](O)=[O:27])=[CH:23][CH:22]=1)([OH:18])=[O:17].CS(O)(=O)=O>C(O)(=O)C>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[O:15][C:26](=[O:27])[CH:25]([C:24]3[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:16]([OH:18])=[O:17])=[CH:31][CH:30]=3)[C:7]=2[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 73112,4-Di-tert-butylphenolHCID 10998701100304-15-2

Product 1

HCID 18961267HCID 18961267, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 20.6 g (0.10 mol) of 2,4-di-tert-butylphenol, 22.6 g (0.10 mol) of 4-carboxymethoxymandelic acid and 1 g (10 mmol) of methanesulfonic acid in 50 ml of acetic acid is refluxed for 15 hours. The acetic acid is then distilled off. The residue is dissolved in 100 ml of dichloromethane, and the solution is washed three times with water. The organic phases are combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from ligroin gives 31.0 g (78%) of 5,7-di-tert-butyl-3-(4-carboxymethoxyphenyl)benzofuran-2-one, melting point 158°-162° C. (Compound (116), Table 1).

Workup

  1. temperatureis refluxed for 15 hours
  2. distillationThe acetic acid is then distilled off
  3. dissolutionThe residue is dissolved in 100 ml of dichloromethane
  4. washthe solution is washed three times with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator
  7. customCrystallisation of the residue from ligroin

Sources & evidence

ORD record
ord-13a59224261d4cdfa6d6ffa72df9e6e5
Source dataset
uspto-grants-1994_10
Patent number
US05356966

Reaction notes

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