4'-Fluoroacetophenone → HCID 12531832, compound

HRID 1981471Notes

Reaction equation

HRID 1981471 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.F[C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 117874-Chloro-1-naphthol

Product 1

HCID 12531832HCID 12531832, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 42.86 g of 4-chloro-1-naphthol, 27.6 g of p-fluoroacetophenone, 33.12 g of potassium carbonate and 200 ml of dimethylacetamide was heated at 150° C., under argon for 18 hours, then poured into ice water, stirred and extracted with ethyl acetate. The extract was washed with 0.5N sodium hydroxide, 0.5N hydrochloric acid, water and brine, dried and evaporated to a residue. This residue was boiled in hexane, then cooled and the intermediate collected to yield the product as white crystals, mp 95°-99° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 0.5N sodium hydroxide, 0.5N hydrochloric acid, water and brine
  3. customdried
  4. customevaporated to a residue
  5. temperaturecooled
  6. customthe intermediate collected

Sources & evidence

ORD record
ord-c4796b3df49149eb9e2aac03242a6c08
Source dataset
uspto-grants-1986_06
Patent number
US04592876

Reaction notes

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