Hydrochloric Acid → HCID 13604200, compound

HRID 414694Notes

Reaction equation

HRID 414694 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[C:6]([CH3:13])[CH:7]=[C:8]([CH3:12])[C:9]=2[OH:11])[CH2:4][CH2:3]1.[C:14]([C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[CH:21]=O)([CH3:17])([CH3:16])[CH3:15].[BH4-].[Na+].Cl.C([O-])(=O)C.[Na+]>C(O)C.O>[C:27]([C:24]1[CH:23]=[C:20]([CH:19]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:25]=1[OH:26])[CH2:21][NH:1][CH:2]1[C:10]2[C:5](=[C:6]([CH3:13])[CH:7]=[C:8]([CH3:12])[C:9]=2[OH:11])[CH2:4][CH2:3]1)([CH3:29])([CH3:30])[CH3:28]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 12857262HCID 12857262, compound

Product 1

HCID 13604200HCID 13604200, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

1.77 Grams of 1-amino-7-hydroxy-4,6-dimethylindane and 50 ml of ethanol solution containing 2.57 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde were stirred together at a room temperature for 2 hours. Then sodium borohydride solution was added gradually by small portions to the reaction mixture under an ice-cooling condition. The reaction mixture was further stirred at a room temperature for 2 hours, then was acidified by adding hydrochloric acid. Then the reaction mixture was concentrated to dryness by evaporating the solvent under a reduced pressure. To the residue obtained was added 100 ml of water, and further added an aqueous solution of sodium acetate to adjust the pH of the solution to about pH=8, then extracted with 100 ml of ethyl acetate. The extract was washed with water, dried with anhydrous magnesium sulfate, concentrated to dryness by evaporating the solvent under a reduced pressure. The residue obtained was dissolved in 50 ml of ethanol, and the pH of the solution was adjusted by adding ethanol saturated with hydrogen chloride gas to about pH=3, then the solution was concentrated to dryness by evaporating the solvent under a reduced pressure. The residue obtained was recrystallized from ether-n-hexane to obtain 0.77 g of 1-(3,5-di-tert-butyl-4-hydroxybenzyl)amino-4,6-dimethyl-7-hydroxyindane in the form of colorless needle-like crystals. Melting point: 154°-155° C.

Workup

  1. temperaturecooling condition
  2. stirringThe reaction mixture was further stirred at a room temperature for 2 hours
  3. concentrationThen the reaction mixture was concentrated to dryness
  4. customby evaporating the solvent under a reduced pressure
  5. customTo the residue obtained
  6. extractionextracted with 100 ml of ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. concentrationconcentrated to dryness
  10. customby evaporating the solvent under a reduced pressure
  11. customThe residue obtained
  12. concentrationthe solution was concentrated to dryness
  13. customby evaporating the solvent under a reduced pressure
  14. customThe residue obtained
  15. customwas recrystallized from ether-n-hexane

Sources & evidence

ORD record
ord-5d6c8995665d458393bdcb1e5d1d2201
Source dataset
uspto-grants-1988_12
Patent number
US04792628

Reaction notes

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