Hydrochloric Acid → 4-[5-(3-Chloro-4-nitro-phenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 537679Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[CH:10]1[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[O:13][C:12]([CH3:20])([CH3:19])[C:11]1=[O:21])[CH3:2].[Cl:22][C:23]1[CH:28]=[C:27](F)[CH:26]=[CH:25][C:24]=1[N+:30]([O-:32])=[O:31].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Cl:22][C:23]1[CH:28]=[C:27]([CH:26]=[CH:25][C:24]=1[N+:30]([O-:32])=[O:31])[O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[C:4]([CH:10]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[O:13][C:12]([CH3:20])([CH3:19])[C:11]2=[O:21])[CH:5]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-(2-ethyl-5-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (100 mg, 0.34 mmol), 2-chloro-4-fluoro-1-nitrobenzene (72 mg, 0.41 mmol), and potassium carbonate (110 mg, 0.69 mmol) in N,N-dimethylformamide (2 ml) is heated to 140° C. under microwave irradiation for 40 minutes. The mixture is cooled to room temperature, poured into 2M aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-[5-(3-chloro-4-nitrophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

temperatureThe mixture is cooled to room temperature
extractionextracted with ethyl acetate
extractionThe organic extract
washis washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customthe filtrate is evaporated under reduced pressure
customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-d36e1300f5f442eb8e6a9a81ab7fc76d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865623B2

Reaction notes

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