Hydrochloric Acid → 2-(4-Fluoro-3-methyl-benzylidene)-hexanoic acid

HRID 1158122Notes

Reaction equation

HRID 1158122 reaction equation
[CH2:1]([CH:5](C(O)=O)[C:6]([OH:8])=[O:7])[CH2:2][CH2:3][CH3:4].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[CH3:21].N1CCCCC1.Cl>N1C=CC=CC=1>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([OH:8])=[O:7])=[CH:15][C:14]=1[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 10801Butylmalonic acidHCID 27348744-Fluoro-3-methylbenzaldehyde

Product 1

HCID 686422372-(4-Fluoro-3-methyl-benzylidene)-hexanoic acidYield 80.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-butyl-malonic acid (2.319 g, 14.482 mmol), 4-fluoro-3-methylbenzaldehyde (1.000 g, 7.241 mmol), and piperidine (1.232 g, 14.482 mmol) in 10 mL of pyridine was heated to 100° C. and stirred at this temperature for 16 h. After cooling to room temperature, the reaction mixture was poured into 25 mL of concentrated HCl containing 50 g of ice, and then extracted with ethyl acetate. The organic extracts were combined and dried over anhydrous Na2SO4, concentrated under reduced pressure, the product isolated by Flash chromatography (silica gel) eluting with 0-30% ethyl acetate/hexanes to give the title compound as yellow liquid (1.370 g, 80% yield). LC-MS: tR=9.5 min; m/z 237 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customthe product isolated by Flash chromatography (silica gel)
  6. washeluting with 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8a8db46ca69c459389743d795b79e907
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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