Benzenepropanal → 1,5-Diphenylpentan-3-ol

HRID 1828065Notes

Reaction equation

HRID 1828065 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([Mg]Br)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>C1COCC1>[C:1]1([CH2:7][CH2:8][CH:9]([OH:10])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7707BenzenepropanalHCID 25517Ammonium ChlorideHCID 178419670HCID 178419670, compound

Product 1

HCID 128385101,5-Diphenylpentan-3-olYield 43.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 12.8 g (95.2 mmol) of 3-phenyl-propionaldehyde in anhydrous THF (100 mL) was added dropwise at 0° C. a 1.0M solution of 100 mL (100 mmol) of phenethyl magnesium bromide in THF, and the mixture was stirred for 2 hours at 0° C. The solution was poured over saturated ammonium chloride and extracted with ether (3×150 mL). The organic phase was dried (MgSO4) and evaporated to a solid, which was subject to column chromatography (EtOAc/Hexanes, 1:9) to yield 10.0 g (22.8%) of 8a as a white solid. TLC Rf=0.5 (EtOAc/Hexanes, 1:9)

Workup

  1. extractionextracted with ether (3×150 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated to a solid, which

Sources & evidence

ORD record
ord-ad87906cf7eb4b038b732488c8c45c72
Source dataset
uspto-grants-2006_06
Patent number
US07056935B2

Reaction notes

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