Hydrochloric Acid → HCID 10707978, compound

HRID 964803Notes

Reaction equation

HRID 964803 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-3f77af7f5736448e9c46454f4c3714ef
Source dataset
uspto-grants-1998_06
Patent number
US05770772

Reaction notes

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