3,3,5-Trimethylcyclohexanol → HCID 67294303, compound

HRID 334830Notes

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.[CH3:20][C:21]1([CH3:29])[CH2:26][CH:25]([CH3:27])[CH2:24][CH:23]([OH:28])[CH2:22]1.[H-].[Na+]>O1CCOCC1>[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH2:17][O:28][CH:23]3[CH2:24][CH:25]([CH3:27])[CH2:26][C:21]([CH3:29])([CH3:20])[CH2:22]3)[C:11]=2[OH:19])[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 (0.8 g, 2.9 mmol) is partly solved in dioxane (23 mL) at 80° C. 3,3,5-Trimethyl-cyclohexanol (12.3 g, 86 mmol) and sodium hydride (200 mg, 5 mmol, 60% in mineral oil) are added subsequently. The orange reaction mixture is stirred at 70° C. for one hour and evaporated to dryness. The residue is dissolved in ethyl acetate and extracted with water. The organic layer is dried over sodium sulphate, filtered and evaporated to dryness. The crude product is purified by column chromatography (ethyl acetate/heptane 1:4) to yield 0.8 g of 2-(2H-Benzotriazol-2-yl)-6-(3,3,5-trimethyl-cyclohexyloxymethyl)-4-methyl-phenol.

Workup

customevaporated to dryness
dissolutionThe residue is dissolved in ethyl acetate
extractionextracted with water
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 1:4)

Sources & evidence

ORD record: ord-e6c43fb0191240869cb25eb55521a5ba
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883829B2

Reaction notes

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