Hydrochloric Acid → 4'-Fluoro-2-phenylacetophenone

HRID 1659553Notes

Reaction equation

HRID 1659553 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:9])=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3182354'-Fluoro-2-phenylacetophenone

Procedure

28.4 g of phenylacetyl chloride was dissolved in 130 ml of fluorobenzene and cooled in ice. This solution was added to 27.0 g of freshly powdered aluminum chloride with continued cooling and stirring. After the vigorous reaction subsided, the mixture was stirred at room temperature overnight and then poured onto 150 g of ice containing 50 ml of concentrated hydrochloric acid. Extraction gave a pale brown solid. Recrystallization from petroleum ether gave 4-fluorodeoxybenzoin, 2A, as a white solid, mp: 80°-81° C.

Workup

  1. temperaturecooled in ice
  2. temperaturewith continued cooling
  3. customAfter the vigorous reaction
  4. stirringthe mixture was stirred at room temperature overnight
  5. extractionExtraction
  6. customgave a pale brown solid
  7. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-15775e255c4f4b94a5869e6f3d600f48
Source dataset
uspto-grants-1981_12
Patent number
US04304789

Reaction notes

Loading…