Sodium hydride → 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-n-dodecylpyrrolidine-2,5-dione

HRID 247611

Reaction equation

HRID 247611 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].[CH2:18]([N:30]1[C:34](=[O:35])[CH:33]=[CH:32][C:31]1=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(O)(C)(C)C>[C:13]([C:9]1[CH:10]=[C:11]([CH:33]2[CH2:32][C:31](=[O:36])[N:30]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:34]2=[O:35])[CH:12]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:8]=1[OH:17])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 314052,6-Di-tert-butylphenolHCID 871911H-Pyrrole-2,5-dione, 1-dodecyl-

Product 1

HCID 141483753-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-n-dodecylpyrrolidine-2,5-dioneYield 17.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol, and 26.54 g (0.1 mol) of N-n-dodecylmaleimide in tert-butyl alcohol. The reaction mixture is concentrated in vacuo and the residue is dissolved in 800 ml of toluene. The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml). The organic phase is dried over anhydrous sodium sulfate. The solvent is removed in vacuo and the residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent) followed by recrystallization from petroleum ether to give 8.15 g (17%) of a white solid: mp 66°-70° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in 800 ml of toluene
  3. extractionThe toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml)
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent)
  7. customfollowed by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-5edf68cb1d704d71b99ccd3a9424cb3d
Source dataset
uspto-grants-1987_11
Patent number
US04709050

Linked notes

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