Water → (2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol

HRID 1850409Notes

Reaction equation

HRID 1850409 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C1(C)C=CC=CC=1.[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([CH2:28][C:29]([CH3:31])=[CH2:30])[C:21]=1[OH:32].O>C(OCC)(=O)C>[CH3:30][C:29]1([CH2:31][OH:9])[CH2:28][C:22]2[C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]([CH3:19])[C:21]=2[O:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 70297m-Chloroperbenzoic acidHCID 10655310Phenol, 2,3,5-trimethyl-6-(2-methyl-2-propenyl)-

Product 1

HCID 11998626(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanolYield 39%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

70% m-chloroperbenzoic acid (1.95 g, 7.89 mmol) was added to a solution of toluene (18 mL) containing 2,3,5-trimethyl-6-(2-methylprop-2-en-1-yl)phenol (1.00 g, 5.26 mmol) synthesized in Reference Example 2, and the mixture was stirred at room temperature for 15 hours. The resulting mixture was poured into water, and extraction was performed using ethyl acetate. The extract was washed with 5% sodium sulfite aqueous solution, saturated sodium bicarbonate water and saturated saline, and dried using anhydrous magnesium sulfate. After that, concentration was performed under reduced pressure, and the residue was dissolved in toluene (10 mL). To this solution, trifluoroacetic acid (0.2 mL) was added, and the mixture was stirred at room temperature for 1 hour. After that, the reaction solution was poured into saturated sodium bicarbonate water, and extraction was performed using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-85/15) to give 420 mg of the title compound (yield: 39%).

Workup

  1. customsynthesized in Reference Example 2
  2. washThe extract was washed with 5% sodium sulfite aqueous solution, saturated sodium bicarbonate water and saturated saline
  3. customdried
  4. concentrationAfter that, concentration
  5. dissolutionthe residue was dissolved in toluene (10 mL)
  6. additionTo this solution, trifluoroacetic acid (0.2 mL) was added
  7. stirringthe mixture was stirred at room temperature for 1 hour
  8. additionAfter that, the reaction solution was poured into saturated sodium bicarbonate water, and extraction
  9. washThe extract was washed with saturated saline
  10. customdried
  11. concentrationfollowed by concentration under reduced pressure
  12. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-85/15)

Sources & evidence

ORD record
ord-081805464a914d6e9ef97ef58fac4390
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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