2-Ethylhexanol → HCID 67294257, compound

HRID 341259Notes

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]([CH:23]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:24][OH:25])[CH3:22].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:25][CH2:24][CH:23]([CH2:21][CH3:22])[CH2:26][CH2:27][CH2:28][CH3:29])[C:10]=3[OH:18])[N:8]=[C:4]2[CH:3]=1

Participants

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 2-ethylhexanol (20.0 g, 154 mmol) and acetone (5 g) and stirred at 80° C. for 15 minutes. Sodium carbonate (3.4 g, 32 mmol) is added. The slightly yellow reaction mixture is stirred at 80° C. for 3 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 4.9 g of 2-(5-Chloro-benzotriazol-2-yl)-6-(2-ethylhexyloxymethyl)-4-methyl-phenol.

Workup

stirringThe slightly yellow reaction mixture is stirred at 80° C. for 3 hours
customevaporated 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-643d5afc7e544ddbb95c4377245c7d0f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895754B2

Reaction notes

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