Hydrochloric Acid → HCID 21848317, compound

HRID 618713Notes

Reaction equation

HRID 618713 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1.[CH:15](=[O:18])[CH2:16][CH3:17].Cl>CCCCCC.O1CCCC1>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[CH:15]([OH:18])[CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 527PropanalHCID 99753-FluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 21848317HCID 21848317, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

66.7 ml (106.8 mmol) of a 1.6N butyllithium solution in hexane were added at -78° to a solution of 12 g (95.14 mmol) of 3-fluoroanisole in 240 ml of anhydrous tetrahydrofuran and the mixture was stirred for one hour. Subsequently, 21 ml (288 mmol) of propionaldehyde were added dropwise thereto at -78°, the mixture was stirred for one hour and the solution was left to come to room temperature. The mixture was poured into 240 ml of 1 N HCl and extracted twice with 250 ml of diethyl ether each time After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane/hexane 1:1). There were obtained 15 g (86%) of 1-(2-fluoro-6-methoxy-phenyl)-propan-1-ol as a pale yellow oil.

Workup

  1. stirringat -78°, the mixture was stirred for one hour
  2. waitthe solution was left
  3. customto come to room temperature
  4. extractionextracted twice with 250 ml of diethyl ether each time
  5. dry with materialAfter drying over sodium sulfate concentration
  6. customThe crude product obtained
  7. customwas purified by column chromatography on silica gel (dichloromethane/hexane 1:1)

Sources & evidence

ORD record
ord-030252e7dcd34d43bde5e7935a5ffbb0
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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