Hydrochloric Acid → HCID 23113866, compound

HRID 2376355Notes

Reaction equation

HRID 2376355 reaction equation
[CH2:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[OH:12])[CH:2]=[CH2:3].Cl.[OH-].[Na+]>CO>[CH3:3][CH:2]1[CH2:1][C:4]2[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=2[O:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2596542-Allyl-3,5-dimethylphenol

Product 1

HCID 23113866HCID 23113866, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-allyl-3,5-dimethylphenol obtained in Reference Example 215 (935 mg, 5.77 mmol) in methanol (5 mL) was added concentrated hydrochloric acid (5 mL), and the mixture was heated under reflux under argon atmosphere for 20 hours. The reaction solution was neutralized by aqueous sodium hydroxide solution, which was extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to obtain the residue, which was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 472 mg (yield 50%) of the title compound. Oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under argon atmosphere for 20 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto obtain the residue, which
  9. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-3901f2db78c94217b306afb948be89e4
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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