Hydrochloric Acid → 2-Methoxy-5-(1,1,2,2,2-pentafluoroethyl)benzaldehyde

HRID 1634336Notes

Reaction equation

HRID 1634336 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[CH:16]1OCCC[O:17]1.Cl>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:14])([F:15])[C:10]([F:11])([F:12])[F:13])=[CH:5][C:4]=1[CH:16]=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18677628HCID 18677628, compound

Product 1

HCID 186776122-Methoxy-5-(1,1,2,2,2-pentafluoroethyl)benzaldehydeYield 33.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of Compound 39 (1.0 g) in acetone (30 ml) was added conc. HCl (4 ml) at room temperature. The reaction mixture was stirred at room temperature for 5 h. The solvent was evaporated in vacuo and the residue was extracted with ether. The combined solution was washed with sat. NaHCO3 aq. , and brine, dried(MgSO4) and concentrated in vacuo to give crude product (790 mg) as a yellow solid. The crude product was purified by column chromatography on silica gel with hexane-isopropyl ether(10:1-3:1) to give Compound 40 (275 mg) as a pale yellow solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionthe residue was extracted with ether
  3. washThe combined solution was washed with sat. NaHCO3 aq. , and brine, dried(MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give crude product (790 mg) as a yellow solid
  6. customThe crude product was purified by column chromatography on silica gel with hexane-isopropyl ether(10:1-3:1)

Sources & evidence

ORD record
ord-700a2257937c400f89997775bfe508d2
Source dataset
uspto-grants-2003_01
Patent number
US06506775B1

Reaction notes

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