Hydrochloric Acid → HCID 86620353, compound

HRID 1669245Notes

Reaction equation

HRID 1669245 reaction equation
C[O:2][CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:5][CH3:6].Cl>C1COCC1>[F:20][C:19]([F:21])([F:22])[C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH:4]([CH2:5][CH3:6])[CH:3]=[O:2])=[CH:8][CH:9]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67341559HCID 67341559, compound

Product 1

HCID 86620353HCID 86620353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(1-methoxymethylenepropyl)-4′-trifluoromethylbiphenyl (278 mg, 0.908 mmol) in THF (9.1 mL) is treated with concentrated hydrochloric acid (0.456 mL), and the reaction is heated at reflux overnight. The reaction mixture is cooled to RT, and extracted with EtOAc (3×). The combined organic layers are dried and concentrated, giving 2-(4′-trifluoromethylbiphenyl-4-yl)butyraldehyde as a crude residue to be used as is (weight in excess of theoretical yield).

Workup

  1. temperaturethe reaction is heated
  2. temperatureat reflux overnight
  3. extractionextracted with EtOAc (3×)
  4. customThe combined organic layers are dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a1032005a29a4d07a6eb7238e7df9fd8
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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