Sodium Hydroxide → Benzofuran, 2,3-dihydro-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-

HRID 1797402Notes

Reaction equation

HRID 1797402 reaction equation
FC(F)(F)S(O)(=O)=O.[CH3:9][C:10]([O:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:23]=1[CH3:30])([CH3:20])[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:9][C:10]1([CH3:20])[CH:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:27]2[C:26]([CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]([CH3:30])[C:22]=2[O:21]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 9944111HCID 9944111, compound

Product 1

HCID 10850374Benzofuran, 2,3-dihydro-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-Yield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoromethanesulfonic acid (7.5 mL) was added to a solution of 2-methyl-1-(4-methylphenyl)-2-(2,3,5-trimethylphenoxy)-1-propanol (253.7 g) obtained in Example 2 in toluene (1260 mL), and the mixture was stirred at 50° C. for 30 minutes and then for 1 hour under reflux. To the mixture was added 1N NaOH (756 mL) at 25° C. The toluene layer was separated and washed with water, and the solvent was distilled off. The residue was dissolved in isopropanol (1511 mL) and water (756 mL) was added thereto. Precipitated crystals were filtered to obtain the title compound (176.33 g, 74%).

Workup

  1. temperaturefor 1 hour under reflux
  2. customThe toluene layer was separated
  3. washwashed with water
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in isopropanol (1511 mL)
  6. additionwater (756 mL) was added
  7. customPrecipitated crystals
  8. filtrationwere filtered

Sources & evidence

ORD record
ord-57282e67dd504871bf1327fcf527d93b
Source dataset
uspto-grants-2006_04
Patent number
US07034166B2

Reaction notes

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