Hydrochloric Acid → HCID 21802780, compound

HRID 2063795Notes

Reaction equation

HRID 2063795 reaction equation
Cl.[CH3:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[C:5]([CH2:11][CH:12]=[CH2:13])[C:4]=1[OH:14].C(=O)([O-])O.[Na+]>C(O)C>[CH3:13][CH:12]1[CH2:11][C:5]2[C:6]([CH3:10])=[CH:7][C:8]([CH3:9])=[C:3]([CH3:2])[C:4]=2[O:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2465702,3,5-Trimethyl-6-(prop-2-en-1-yl)phenolHCID 516892Sodium Bicarbonate

Product 1

HCID 21802780HCID 21802780, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated hydrochloric acid (130 mL) was added to a solution of ethanol (520 mL) containing 2,3,5-trimethyl-6-prop-2-en-1-ylphenol (52.0 g, 295 mmol) synthesized in Reference Example 51, and the mixture was heated to reflux for 16 hours. The reaction solution was neutralized with a sodium hydrogencarbonate aqueous solution, and then the mixture was extracted using ethyl acetate. The organic layer was washed with saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5) to give 35.7 g of the title compound as an oily product (yield: 69%).

Workup

  1. customsynthesized in Reference Example 51
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 16 hours
  4. extractionthe mixture was extracted
  5. washThe organic layer was washed with saturated saline
  6. customdried
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5)

Sources & evidence

ORD record
ord-6e13cc46cd344970bc4fc3441fb2e180
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

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