Hydrochloric Acid → (4'-Trifluoromethyl-biphenyl-4-yl)-acetaldehyde

HRID 1669233Notes

Reaction equation

HRID 1669233 reaction equation
C[O:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.Cl.CCOC(C)=O.CCCCCC>C1COCC1>[F:18][C:17]([F:19])([F:20])[C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][CH:3]=[O:2])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 67343516HCID 67343516, compound

Product 1

HCID 59729427(4'-Trifluoromethyl-biphenyl-4-yl)-acetaldehydeYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 4′-(2-methoxy-vinyl)-4-trifluoromethyl-biphenyl (464 mg, 1.67 mmol) in THF (17 mL) is added dropwise concentrated hydrochloric acid (2.98 mL) and the reaction is warmed to room temperature. After 1 h TLC (30% EtOAc/hexane) indicates complete consumption of starting material. The reaction mixture is diluted with water and the pH is adjusted to 8 with solid NaHCO3. The reaction mixture is concentrated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (40 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (424 mg, 96%). 1NMR (400 MHz, CDCl3) δ ppm: 9.81 (t, 1H, J=2.2 Hz), 7.69 (s, 4H), 7.61 (d, 2H, J=8.4 Hz), 7.33 (d, 2H, J=8.4 Hz), 3.78 (d, 2H, J=1.8 Hz).

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture is diluted with water
  3. concentrationThe reaction mixture is concentrated
  4. extractionthe aqueous layer extracted with EtOAc (3×50 mL)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (40 g SiO2, 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-65f51757dc63418fa8098b339ae53222
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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