Sodium Carbonate → HCID 67294339, compound

HRID 341262Notes

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.[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+]>O1CCCC1>[N:1]1[N:2]([C:10]2[C:11]([OH:19])=[C:12]([CH:13]=[C:14]([CH3:16])[CH:15]=2)[CH2:17][O:21][C:20](=[O:23])[CH2:11][CH:12]([CH3:17])[CH3:13])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 70 °C

Procedure

2-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol (10.0 g, 33 mmol) is suspended in a mixture of 2-isovaleric acid (8.4 g, 82 mmol) and tetrahydrofuran (75 g) and stirred at 70° C. for 30 minutes. Sodium carbonate (10.5 g, 99 mmol) is added. The reaction mixture is stirred at 60° C. for 15 minutes and evaporated to dryness. The residue is dissolved in ethyl acetate and extracted with an aqueous potassium carbonate solution (10%) 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 11.5 g of 3-Methyl-butyric acid 3-(2H-benzotriazol-2-yl)-2-hydroxy-5-methyl-benzyl ester.

Workup

stirringThe reaction mixture is stirred at 60° C. for 15 minutes
customevaporated to dryness
dissolutionThe residue is dissolved in ethyl acetate
extractionextracted with an aqueous potassium carbonate solution (10%) 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-3830a50cd3564eb1921e55226dbf66ee
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895754B2

Reaction notes

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