Potassium Hydroxide → HCID 19741658, compound

HRID 2255200Notes

Reaction equation

[CH2:1]([C:4]1[C:5]([OH:13])=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3].[F:14][C:15]1[C:20]([C:21](Cl)=O)=[C:19]([F:24])[C:18]([F:25])=[C:17]([F:26])[C:16]=1[F:27].[OH-].[K+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH2:1]([C:4]1[C:5]2[O:13][C:21]([C:20]3[C:19]([F:24])=[C:18]([F:25])[C:17]([F:26])=[C:16]([F:27])[C:15]=3[F:14])=[CH:11][C:10](=[O:12])[C:6]=2[CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 19 g (mmol) 3'-allyl-2'-hydroxyacetophenone, 25 g (110 mmol) pentafluorobenzoyl chloride, 36 g (110 mmol) tetra-n-butylammonium bisulfate, 750 ml 10% aqueous KOH, and 750 ml benzene was heated at 80° C. for 6 hours, cooled and the phases separated. The organic phase was concentrated in vacuo and flash chromatographed over 100 g silica gel with success, 2 liter portions of hexane, diethyl ether and CHCl3. The diethyl ether eluate was evaporated in vacuo. The residue was dissolved in 250 ml methanol and cooled at -20° C. for 24 hours. The mixture was filtered and yielded 8-allyl-2-(pentafluorophenyl)-4H-benzopyran-4-one as 10.141 g (27%) solid: TLC Rf 0.35 in 49:25:25:1 CHCl3 :toluene:hexane:methanol.

Workup

temperaturecooled
customthe phases separated
concentrationThe organic phase was concentrated in vacuo and flash
customchromatographed over 100 g silica gel with success, 2 liter portions of hexane, diethyl ether and CHCl3
customThe diethyl ether eluate was evaporated in vacuo
dissolutionThe residue was dissolved in 250 ml methanol
temperaturecooled at -20° C. for 24 hours
filtrationThe mixture was filtered

Sources & evidence

ORD record: ord-8aa5ecced66740dd9e7106b78e56208b
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05238954

Reaction notes

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