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3,5,5-Trimethyl-1-hexanol → 2-(2H-Benzotriazol-2-yl)-4-methyl-6-(3,5,5-trimethylhexyloxymethyl)-phenol

HRID 334829
Notes
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Reaction equation

HRID 334829 reaction equation
[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH2:17]Cl)[C:11]=2[OH:19])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH3:20][CH:21]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:23][OH:24].[H-].[Na+]>O1CCOCC1>[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH2:17][O:24][CH2:23][CH2:22][CH:21]([CH3:20])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11]=2[OH:19])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 189383,5,5-Trimethyl-1-hexanolHCID 24758Sodium hydrideHCID 547519482-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol

Product 1

HCID 672943312-(2H-Benzotriazol-2-yl)-4-methyl-6-(3,5,5-trimethylhexyloxymethyl)-phenolYield 49.1%

Reagents, catalysts & solvents 1

HCID 312751,4-Dioxane
Solvent

Conditions

Temperature
80 °C

Procedure

2-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol (7.0 g, 25.6 mmol) is partly solved in dioxane (190 mL) at 80° C. 3,5,5-Trimethyl-hexan-1-ol (124.1 g, 731 mmol) and sodium hydride (1.7 g, 42 mmol, 60% in mineral oil) are added subsequently. The orange reaction mixture is stirred at 80° C. for one hour and evaporated to dryness. The residue is dissolved in ethyl acetate and extracted with water. 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 4.8 g of 2-(2H-Benzotriazol-2-yl)-4-methyl-6-(3,5,5-trimethylhexyloxymethyl)-phenol.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. extractionextracted with water
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product is purified by column chromatography (ethyl acetate/heptane 1:12)

Sources & evidence

ORD record
ord-14eba43c76054600818d4866d6213859
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883829B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes