Diethyl Ether → 1-(4-Biphenyl)-1-propanol

HRID 1485087Notes

Reaction equation

HRID 1485087 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15](OCC)[CH3:16]>C([Mg]Br)C>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][C:10]([CH:11]([OH:12])[CH2:15][CH3:16])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Product 1

HCID 131304821-(4-Biphenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 178418443HCID 178418443, compoundSolvent

Procedure

To a solution of 4-phenylbenzaldehyde (1.20 g) in diethyl ether (13.2 mL), ethylmagnesium bromide (about 3.0 mol/L, solution in diethyl ether, 3.29 mL) was added at 0° C. After stirring the mixture at room temperature for 3 hours, the precipitate was recovered by filtration. After dissolving the recovered precipitate in a liquid mixture of ethyl acetate and a saturated aqueous solution of ammonium chloride, three extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine. After passage through a phase separator, the washed organic layers were concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-70:30) to give 1-(biphenyl-4-yl)propan-1-ol as a colorless solid (1.27 g).

Workup

  1. filtrationthe precipitate was recovered by filtration
  2. dissolutionAfter dissolving the recovered precipitate
  3. additionin a liquid mixture of ethyl acetate
  4. extractiona saturated aqueous solution of ammonium chloride, three extractions
  5. washThe combined organic layers were washed with saturated brine
  6. concentrationAfter passage through a phase separator, the washed organic layers were concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-70:30)

Sources & evidence

ORD record
ord-6fbd659146bb425bb0d00c63a10a5ecf
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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