Acetic Acid → 2-Fluoro-1-phenylethan-1-one

HRID 2293878Notes

Reaction equation

HRID 2293878 reaction equation
[F:1][C:2]1C=CC(C=O)=CC=1.[CH:10]1([C:13](=O)[CH2:14][C:15]([O:17]CC)=O)[CH2:12][CH2:11]1.N1CCCC[CH2:22]1.CC(O)=O>C1C=CC=CC=1.CCOCC.O>[F:1][CH2:2][C:15]([C:14]1[CH:22]=[CH:11][CH:12]=[CH:10][CH:13]=1)=[O:17]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 680234-FluorobenzaldehydeHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoate

Product 1

HCID 99472-Fluoro-1-phenylethan-1-oneYield 82%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-fluorobenzaldehyde (4.768 gm, 38.4 mmol), ethyl 3-cyclopropyl-3-oxopropionate from Example 88, part A (6.000 gm, 38.4 mmol), piperidine (380 μl), and HOAc (75 μl) was refluxed in benzene (40 ml) with removal of water (Dean-Stark trap) for 16 hours. The cooled mixture was diluted with Et2O and washed successively with 5% HCl, saturated NaHCO3, H2O, and brine, then dried (Na2 SO4), filtered, and stripped to yield an oil. Distillation of the oil (bp 127°-135° C. at 0.2 mm Hg) afforded compound A (8.299 gm, 82%) as a pale yellow liquid.

Workup

  1. washwashed successively with 5% HCl, saturated NaHCO3, H2O, and brine
  2. customdried (Na2 SO4)
  3. filtrationfiltered
  4. customto yield an oil
  5. distillationDistillation of the oil (bp 127°-135° C. at 0.2 mm Hg)

Sources & evidence

ORD record
ord-b0cb803ccf5540feadcac35103984ae7
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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