Hydrochloric Acid → HCID 23442854, compound

HRID 2119731Notes

Reaction equation

HRID 2119731 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([O:14]C(=O)C)=[CH:7][C:6]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:3])[CH3:2].Cl>CO>[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([OH:14])=[CH:7][C:6]=1[C:18]([CH3:19])([CH3:20])[CH3:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23442894HCID 23442894, compound

Product 1

HCID 23442854HCID 23442854, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.10 g of 1,4-diacetoxy-2-t-butyl-6-isopropylbenzene was dissolved in 22 ml of methanol, 2.5 ml of 3N hydrochloric acid was added, and the solution was heated under reflux for 2.5 hours. After cooling to room temperature, methanol was distilled off on a rotary evaporator. The concentrate was combined with water and extracted with ethyl acetate. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 5%-10% ethyl acetate) to give 0.66 g of 4-acetoxy-3-t-butyl-5-isopropylphenol as a pale yellow solid (yield 70%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2.5 hours
  3. distillationmethanol was distilled off on a rotary evaporator
  4. extractionextracted with ethyl acetate
  5. washThe organic layers were washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 5%-10% ethyl acetate)

Sources & evidence

ORD record
ord-03594c7ba71340b7a4cea3ed6ea3a4eb
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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