Sodium Hydroxide → 3-(3,5-DI-Tert-butyl-4-hydroxy-benzyl)-pentane-2,4-dione

HRID 1263348Notes

Reaction equation

HRID 1263348 reaction equation
CN([CH2:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)C.[OH-].[Na+].[C:22]([CH2:25][C:26](=[O:28])[CH3:27])(=[O:24])[CH3:23]>>[C:16]([C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]=1[OH:15])[CH2:4][CH:25]([C:26](=[O:28])[CH3:27])[C:22](=[O:24])[CH3:23])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 31261AcetylacetoneHCID 66609Phenol, 4-[(dimethylamino)methyl]-2,6-bis(1,1-dimethylethyl)-

Product 1

HCID 9144013-(3,5-DI-Tert-butyl-4-hydroxy-benzyl)-pentane-2,4-dioneYield 97%

Procedure

A mixture of the N,N-dimethyl-2,6-di-t-butyl-4-aminomethylphenol (10.5 g, 40 mmols), sodium hydroxide (1.8 g, 45 mmols) and acetylacetone (24 mLs, 10% solution) was refluxed for 3 hours. Acetylacetone was distilled under reduced pressure to afford an oily residue of the 3-(3',5'-di-t-butyl-4'-hydroxybenzyl)-2,4-pentanedione compound (97% by VPC).

Workup

  1. temperaturewas refluxed for 3 hours
  2. distillationAcetylacetone was distilled under reduced pressure

Sources & evidence

ORD record
ord-dee4cc2ee362478f8caf5f9fb4fa010f
Source dataset
uspto-grants-1984_06
Patent number
US04456770

Reaction notes

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