Hydrogen Peroxide → HCID 86663662, compound

HRID 1193217Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[C:10]([CH:18]=[C:19]3[C:23]([CH3:25])([CH3:24])[O:22][C:21]([CH3:27])([CH3:26])[C:20]3=[O:28])[CH:9]=2)=[CH:4][CH:3]=1.[OH:29]O.[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[C:10]([CH:18]3[C:19]4([C:20](=[O:28])[C:21]([CH3:27])([CH3:26])[O:22][C:23]4([CH3:24])[CH3:25])[O:29]3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of 4-[1-(4′-chloro-4-trifluoromethylbiphenyl-3-yl)methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (2.50 g, 6.12 mmol) in methanol (75 ml) at 35 ° C. is added 50% aqueous hydrogen peroxide solution (0.70 ml, 12.2 mmol), followed immediately by a solution of 2M aqueous lithium hydroxide (0.76 ml, 1.52 mmol). This mixture is stirred at 35° C. for 45 minutes, then allowed to cooled to room temperature and quenched with saturated sodium metabisulfite solution. The crude product is extracted with diethyl ether (×2), then all organics are combined and dried over magnesium sulfate. After filtration the filtrate is concentrated in vacuo to afford 2-(4′-chloro-4-trifluoromethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (2.59 g) as a yellow gum. This material is used directly in the next step.

Workup

temperatureto cooled to room temperature
customquenched with saturated sodium metabisulfite solution
extractionThe crude product is extracted with diethyl ether (×2)
dry with materialdried over magnesium sulfate
filtrationAfter filtration the filtrate
concentrationis concentrated in vacuo

Sources & evidence

ORD record: ord-3538598b1d81404ebd64b1e621f591ac
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680299B2

Reaction notes

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