Sodium hydride → 2-(2H-Benzotriazol-2-yl)-6-(3-methyl-butoxymethyl)-4-(1,1,3,3-tetramethyl-butyl)-phenol

HRID 334841Notes

Reaction equation

HRID 334841 reaction equation
[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([C:16]([CH3:23])([CH3:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=[C:12]([CH2:24]Cl)[C:11]=2[OH:26])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:27]([OH:32])[CH2:28][CH:29]([CH3:31])[CH3:30].[H-].[Na+]>>[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([C:16]([CH3:23])([CH3:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=[C:12]([CH2:24][O:32][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:11]=2[OH:26])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 31260Isoamyl AlcoholHCID 682731732-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-(1,1,3,3-tetramethyl-butyl)-phenol

Product 1

HCID 682731742-(2H-Benzotriazol-2-yl)-6-(3-methyl-butoxymethyl)-4-(1,1,3,3-tetramethyl-butyl)-phenolYield 64.7%

Conditions

Temperature
80 °C

Procedure

2-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-(1,1,3,3-tetramethyl-butyl)-phenol (5.0 g, 13.5 mmol) is suspended in isoamyl alcohol (20.0 g, 227 mmol) and stirred at 80° C. for 15 minutes. Sodium hydride (0.2 g, 4.3 mmol, 60% in mineral oil) is added. The orange reaction mixture is stirred at 80° C. for 15 minutes and evaporated to dryness. The residue is dissolved in ethyl acetate and extracted with aqueous citric acid (5%) and brine. The organic layer is dried over sodium sulphate, filtered and evaporated to dryness. The crude product is purified by column chromatography (ethyl acetate/heptane 1:12) to yield 3.7 g of 2-(2H-Benzotriazol-2-yl)-6-(3-methyl-butoxymethyl)-4-(1,1,3,3-tetramethyl-butyl)-phenol.

Workup

  1. stirringThe orange reaction mixture is stirred at 80° C. for 15 minutes
  2. customevaporated to dryness
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. extractionextracted with aqueous citric acid (5%) and brine
  5. dry with materialThe organic layer is dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product is purified by column chromatography (ethyl acetate/heptane 1:12)

Sources & evidence

ORD record
ord-e831dd8c9c98487ea53077ea63b60ef0
Source dataset
uspto-grants-2014_11
Patent number
US08883829B2

Reaction notes

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