Hydrochloric Acid → HCID 10707978, compound

HRID 234265Notes

Reaction equation

HRID 234265 reaction equation
[CH3:1][C:2]1[C:3]([CH2:18][C:19]([CH3:21])=[CH2:20])=[C:4]([OH:17])[C:5]([CH3:16])=[C:6]([CH3:15])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:20][C:19]1([CH3:21])[CH2:18][C:3]2[C:2]([CH3:1])=[C:7]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([CH3:15])=[C:5]([CH3:16])[C:4]=2[O:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10850422HCID 10850422, compound

Product 1

HCID 10707978HCID 10707978, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5,6-trimethyl-2-(2-methyl-2-propenyl)-4-phenylaminophenol (1.40 g, 4.98 mmol) in methanol (30 ml) was added conc. hydrochloric acid (10 ml) with ice-cooling and the mixture was heated with reflux in an argon atmosphere. The reaction mixture was cooled, neutralized with an aqueous sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed with a saturated saline solution and concentrated. The residue was recrystallized from isopropyl ether to obtain the desired compound (0.97 g, yield: 69.3%), m.p. 148°-150° C.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperaturewith reflux in an argon atmosphere
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated saline solution
  7. concentrationconcentrated
  8. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-d744232cb9e146dcb06850bb84ef4d5f
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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