Potassium Acetate → HCID 19025555, compound

HRID 1033425Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=[O:17])[CH2:15]Br)=[CH:4][CH:3]=1.[C:18]([O-:21])(=[O:20])[CH3:19].[K+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=[O:17])[CH2:15][O:21][C:18](=[O:20])[CH3:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1.44 g (4.98 mmol) of 4'-methyl-2-(bromoacetyl)-1,1'-biphenyl in 3.0 mL of polyehtyleneglycol-400 was added to a solution of 500 mg of potassium acetate in 3.0 mL of polyethyleneglycol-400. The suspension was heated at 100° C. for 30 minutes, then cooled and diluted with 100 mL of water. The resultant mixture was extracted with ether; the combined ether extracts were diluted with an equal volume of hexane and washed with water. The organic layer was separated, dried over magnesium sulfate, filtered, and the solvent was removed under vacuum to yield an oil which was purified by silica chromatography, eluting with hexane/ethyl acetate (8:1) to give 444 mg (1.66 mmol, 33%) of product as an oil. 1H NMR (200 MHz,CDCl3): 2.06 (s,3H), 2.39 (s,3H), 4.46 (s,2H), 7.23 (s,4H), 7.3-7.6 (m,4H).

Workup

temperaturecooled
extractionThe resultant mixture was extracted with ether
additionthe combined ether extracts were diluted with an equal volume of hexane
washwashed with water
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
customthe solvent was removed under vacuum
customto yield an oil which
customwas purified by silica chromatography
washeluting with hexane/ethyl acetate (8:1)

Sources & evidence

ORD record: ord-7d3692dbe18e4aba9a0d0ad1719561e5
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05310737

Reaction notes

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