Methanesulfonic Acid → HCID 10297662, compound

HRID 2380723Notes

Reaction equation

HRID 2380723 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:8][C:9]1[CH:10]=[C:11]([CH:17]2[C:21]3[CH:22]=[C:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=[C:25]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]=3[O:19][C:18]2=[O:34])[CH:12]=[C:13]([CH3:16])[C:14]=1[OH:15].CS(O)(=O)=O>C1(C)C(C)=CC=CC=1>[CH3:8][C:9]1[CH:10]=[C:11]([CH:17]2[C:21]3[CH:22]=[C:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=[C:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[C:20]=3[O:19][C:18]2=[O:34])[CH:12]=[C:13]([CH3:16])[C:14]=1[O:15][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 62493Pivaloyl chlorideHCID 111006493-(4-Hydroxy-3,5-dimethylphenyl)-5,7-bis(2-methyl-2-propanyl)-1-benzofuran-2(3H)-one2×

Product 1

HCID 10297662HCID 10297662, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

180.1 g (1.49 mol) of pivaloyl chloride are added dropwise over a period of 25 minutes to a suspension of 274.5 g (0.75 mol) of 3-(3,5-dimethyl-4-hydroxyphenyl)-5,7-di-tert-butylbenzofuran-2-one, (compound (107), Table 1, Example 2) in 600 ml of xylene and 7.5 ml (115.7 mmol) of methanesulfonic acid which is stirred at 95° C. under a nitrogen atmosphere. The clear, homogeneous reaction mixture is then refluxed for another 2.5 hours and then concentrated under a slight vacuum. 50 ml of 1-butanol and 600 ml of methanol are carefully poured into the liquid, hot residue at about 170° C. through the condenser and the mixture is cooled with ice/water. The precipitated product is filtered and washed with 350 ml of cold methanol. Drying gives 311.9 g (92%) of 3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one, melting point 140°-142° C. (compound (110 ), Table 1).

Workup

  1. temperatureThe clear, homogeneous reaction mixture is then refluxed for another 2.5 hours
  2. concentrationconcentrated under a slight vacuum
  3. addition50 ml of 1-butanol and 600 ml of methanol are carefully poured into the liquid, hot residue at about 170° C. through the condenser
  4. temperaturethe mixture is cooled with ice/water
  5. filtrationThe precipitated product is filtered
  6. washwashed with 350 ml of cold methanol
  7. customDrying

Sources & evidence

ORD record
ord-d8ce0056a0a34c3bb30cff2854564c70
Source dataset
uspto-grants-1994_11
Patent number
US05369159

Reaction notes

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