Sodium Hydroxide → HCID 22407754, compound

HRID 439686Notes

Reaction equation

HRID 439686 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[C:8]([C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[C:15](Cl)=[O:16])([CH3:11])([CH3:10])[CH3:9].[OH-].[Na+]>C(Cl)Cl.O>[C:22]([C:19]1[CH:18]=[C:14]([CH:13]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:20]=1[OH:21])[C:15]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])=[O:16])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 766463-(Dimethylamino)-1-propanolHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 22407754HCID 22407754, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 41.3 g (400 mmol) of 3-dimethylaminopropanol in 200 ml of methylene chloride was added to a solution of 107.3 g (400 mmol) of 3,5-di-tert-butyl-4-hydroxybenzoyl chloride prepared as described in Example 1 in 400 ml of methylene chloride over a period of seven minutes. The reaction was exothermic. The reaction mixture was stirred for 90 minutes at room temperature and then washed with a solution of 16.0 g (400 mmol) of NaOH in 600 ml of water and then with water. The solution was dried over magnesium sulfate and concentrated to a residue on a rotary evaporator. The residue was then heated to reflux in 800 ml of heptane and filtered through supercel. The filtrate was cooled and the white solid was collected, washed with heptane and dried to give 92.3 g (68.8% of theory) of 3-dimethylaminopropyl 3,5-di-tert-butyl-4-hydroxybenzoate.

Workup

  1. customprepared
  2. dry with materialThe solution was dried over magnesium sulfate
  3. concentrationconcentrated to a residue on a rotary evaporator
  4. temperatureThe residue was then heated
  5. temperatureto reflux in 800 ml of heptane
  6. filtrationfiltered through supercel
  7. temperatureThe filtrate was cooled
  8. customthe white solid was collected
  9. washwashed with heptane
  10. customdried

Sources & evidence

ORD record
ord-a964bfda231c47d0acee1c695e80fef6
Source dataset
uspto-grants-1996_05
Patent number
US05516616

Reaction notes

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