Sodium Carbonate → 2-(2H-Benzotriazol-2-yl)-6-(3-methyl-butoxymethyl)-4-methyl-phenol

HRID 341258Notes

Reaction equation

HRID 341258 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:25])[CH2:21][CH:22]([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH2:17][O:25][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[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 10340Sodium CarbonateHCID 31260Isoamyl AlcoholHCID 547519482-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol

Product 1

HCID 672943332-(2H-Benzotriazol-2-yl)-6-(3-methyl-butoxymethyl)-4-methyl-phenolYield 65.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

2-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol (10.0 g, 33 mmol) is suspended in a mixture of isoamyl alcohol (35 g, 0.4 mol) and acetone (5 g) and stirred at 80° C. for 30 minutes. Sodium carbonate (4.7 g, 44 mmol) is added and the slightly yellow reaction mixture is stirred at 80° C. for 30 minutes. Acetone is removed under vacuum, salts are filtered off and the reaction mixture is 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 7.0 g of 2-(2H-Benzotriazol-2-yl)-6-(3-methyl-butoxymethyl)-4-methyl-phenol.

Workup

  1. stirringthe slightly yellow reaction mixture is stirred at 80° C. for 30 minutes
  2. customAcetone is removed under vacuum, salts
  3. filtrationare filtered off
  4. customthe reaction mixture is evaporated to dryness
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. extractionextracted with aqueous citric acid (5%) and brine
  7. dry with materialThe organic layer is dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe crude product is purified by column chromatography (ethyl acetate/heptane 1:12)

Sources & evidence

ORD record
ord-1c97666c35f74fca92f03aaa3edfb88f
Source dataset
uspto-grants-2014_11
Patent number
US08895754B2

Reaction notes

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