4-Phenylbutanal → 1,7-Diphenyl-4-heptanol

HRID 879

Reaction equation

HRID 879 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1([CH2:18][CH2:19][CH2:20][Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([OH:11])[CH2:20][CH2:19][CH2:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 290304-PhenylbutanalHCID 178418471HCID 178418471, compound

Product 1

HCID 105398701,7-Diphenyl-4-heptanolYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 700 mg (4.7 mmol) of 4-phenyl-1-butanal (119) in 5.0 mL of THF at 0° C. was added 10.0 mL (5.0 mmol) of 3-phenyl-1-propylmagnesium bromide (120) and the resulting mixture was stirred at 0° C. for 0.5 h. The mixture was then quenched by the dropwise addition of saturated NH4Cl and diluted with ether. The phases were separated and the organic layer was washed with water and brine and then dried over MgSO4. Concentration gave 1.12 g of the alcohol 121 as an oil. 1H NMR spectrum was consistent with the structure.

Workup

  1. customThe mixture was then quenched by the dropwise addition of saturated NH4Cl
  2. additiondiluted with ether
  3. customThe phases were separated
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationConcentration

Sources & evidence

ORD record
ord-76f829bb3ada43dbb9e69131f368da79
Source dataset
uspto-grants-1998_03
Patent number
US05723459

Linked notes

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