1-Hexanol → HCID 67294313, compound

HRID 334833Notes

Reaction equation

HRID 334833 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.[CH2:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[H-].[Na+]>O1CCOCC1>[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH2:17][O:26][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]=2[OH:19])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 81031-HexanolHCID 24758Sodium hydrideHCID 547519482-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol

Product 1

HCID 67294313HCID 67294313, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol (1.0 g, 3.2 mmol) is partly solved in dioxane (19 g) at 80° C. and 1-hexanol (6.6 g, 65 mmol) and sodium hydride (0.2 g, 4.3 mmol, 60% in mineral oil) are added subsequently. The orange reaction mixture is stirred at 80° C. for 2 hours 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 1:30) to yield 940 mg of 2-(2H-Benzotriazol-2-yl)-6-hexyloxymethyl-4-methyl-phenol.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. extractionextracted with aqueous citric acid (5%) and brine
  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 1:30)

Sources & evidence

ORD record
ord-60f5a6f65b844e31a5adae239c4cafcb
Source dataset
uspto-grants-2014_11
Patent number
US08883829B2

Reaction notes

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