Sodium Hydroxide → 2,2,4,6,7-Pentamethyl-2,3-dihydrobenzofuran

HRID 1850370Notes

Reaction equation

HRID 1850370 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH2:10][C:11]([CH3:13])=[CH2:12])[C:3]=1[OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:12][C:11]1([CH3:13])[CH2:10][C:4]2[C:5]([CH3:9])=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[C:3]=2[O:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 10655310Phenol, 2,3,5-trimethyl-6-(2-methyl-2-propenyl)-

Product 1

HCID 117454372,2,4,6,7-Pentamethyl-2,3-dihydrobenzofuranYield 85.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,3,5-trimethyl-6-(2-methylprop-2-en-1-yl)phenol (13.0 g, 68.3 mmol) synthesized in Reference Example 2, p-toluenesulfonic acid monohydrate (1.30 g, 6.83 mmol) and toluene (130 mL) was stirred under heated reflux for 1.5 hours. After cooled to room temperature, the reaction solution was distributed by addition of 1N sodium hydroxide aqueous solution. The organic layer was washed with 1N sodium hydroxide aqueous solution and saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by basic silica gel chromatography (hexane-ethyl acetate 49:1 to 24:1) to give 11.1 g of the title compound (yield: 85%).

Workup

  1. temperatureunder heated
  2. temperaturereflux for 1.5 hours
  3. washThe organic layer was washed with 1N sodium hydroxide aqueous solution and saturated saline
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by basic silica gel chromatography (hexane-ethyl acetate 49:1 to 24:1)

Sources & evidence

ORD record
ord-47396749364f4795854d7b5966adcde1
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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