Sodium Carbonate → HCID 67294792, compound

HRID 334838Notes

Reaction equation

HRID 334838 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH2:16]Cl)[C:10]=3[OH:18])[N:8]=[C:4]2[CH:3]=1.[CH2:21]([OH:26])[CH2:22][CH:23]([CH3:25])[CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH2:16][O:26][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:10]=3[OH:18])[N:8]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31260Isoamyl AlcoholHCID 67294335HCID 67294335, compound

Product 1

HCID 67294792HCID 67294792, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

2-(5-Chloro-2H-benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol (5.0 g, 16 mmol) is suspended in a mixture of isoamyl alcohol (20.0 g, 227 mmol) and acetone (5 g) and stirred at 80° C. for 15 minutes. Sodium carbonate (2.1 g, 20 mmol) is added. The slightly yellow 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 1:12) to yield 4.7 g of 2-(5-Chloro-2H-benzotriazol-2-yl)-4-methyl-6-(3-methyl-butoxymethyl)-phenol.

Workup

  1. stirringThe slightly yellow reaction mixture is stirred at 80° C. for 2 hours
  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-45f4eb8947dd486aa3b85183041213af
Source dataset
uspto-grants-2014_11
Patent number
US08883829B2

Reaction notes

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