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

HRID 2293880Notes

Reaction equation

HRID 2293880 reaction equation
[F:1][C:2]1C=CC(C=O)=CC=1.N1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH3:16][C:17]([OH:19])=O.O>C1C=CC=CC=1.CCOCC>[F:1][CH2:2][C:17]([C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8082PiperidineHCID 680234-Fluorobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-fluorobenzaldehyde (4.768 g, 38.4 mmol), the compound from Example 95, part A (6.000 g, 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 (Na2SO4), filtered, and stripped to yield an oil. Distillation of the oil (bp 127°-135° C. at 0.2 mm Hg) afforded compound A (9.299 g, 82%) as a pale yellow liquid.

Workup

  1. washwashed successively with 5% HCl, saturated NaHCO3, H2O, and brine
  2. dry with materialdried (Na2SO4)
  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-7c7b5cb143a14d0dbd829b15994e2c60
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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