Hydrochloric Acid → 2(3H)-Benzofuranone, 5,7-bis(1,1-dimethylethyl)-3-(3,4-dimethylphenyl)-

HRID 1356562Notes

Reaction equation

HRID 1356562 reaction equation
Cl.N[C:3]1[O:4][C:5]2[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][C:17]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:16][C:6]=2[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1.C[OH:29]>O>[C:24]([C:17]1[CH:18]=[C:19]([C:20]([CH3:22])([CH3:23])[CH3:21])[C:5]2[O:4][C:3](=[O:29])[CH:7]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=3)[C:6]=2[CH:16]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18509162HCID 18509162, compound2×

Product 1

HCID 99503072(3H)-Benzofuranone, 5,7-bis(1,1-dimethylethyl)-3-(3,4-dimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.35 ml (0.70 mmol) of 2N HCl is added at room temperature to a solution of 0.22 g (0.63 mmol) of 2-amino-5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-benzofurane [compound (302), Table 3, prepared according to Example 2a] in 5 ml methanol and stirred at room temperature for 2 hours. The reaction mixture is diluted with water and extracted three times with ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated using a vacuum rotary evaporator. Crystallisation of the residue from ethanol yields 200 mg (96%) of 5,7-di-tert-butyl-3-(3,4-dimethylphenyl-3H-benzofuran-2-one (compound (102), Table 1), m.p. 130-132° C.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customa vacuum rotary evaporator
  5. customCrystallisation of the residue from ethanol

Sources & evidence

ORD record
ord-a4e3969a16bd46d8b395aa2cb90ec9b1
Source dataset
uspto-grants-2003_07
Patent number
US06586606B2

Reaction notes

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