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

HRID 334832Notes

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

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 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

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

Sources & evidence

ORD record: ord-c4ffbd2ddb9344eaa3a931eb97543f8f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883829B2

Reaction notes

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