p-tert-Butylacetophenone → 1-(4-Tert-butylphenyl)-3-hydroxy-3-(4-methoxyphenyl)propan-1-one

HRID 603361Notes

Reaction equation

HRID 603361 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1.[NH4+].[Cl-]>C1COCC1>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]([OH:29])[CH2:20][C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[CH:18][CH:17]=2)=[O:21])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 13669p-tert-ButylacetophenoneHCID 25517Ammonium ChlorideHCID 312444-MethoxybenzaldehydeHCID 2724682Lithium diisopropylamide

Product 1

HCID 248151381-(4-Tert-butylphenyl)-3-hydroxy-3-(4-methoxyphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3.4 ml of LDA (lithium diisopropylamide) 1M in THF (3.4 mmol) are added under nitrogen to a solution of p-tert-butylacetophenone (500 mg, 2.8 mmol) in THF (15 ml) at −78° C. The mixture is stirred for 1 h before 5 ml of a THF solution of p-methoxybenzaldehyde (425 mg, 3.1 mmol) are added. The reaction is allowed to reach -400C over the course of 1 h. A cold aqueous solution of NH4Cl 1N is subsequently added to the reaction mixture. The resultant mixture is partitioned between water (30 ml) and dichloromethane (30 ml). The resultant aqueous phase is subsequently extracted with dichloromethane (2×30 ml). The combined organic phases are dried over MgSO4. Removal of the solvent gives 3-(4-methoxyphenyl)-3-hydroxy-1-(4-tert-butylphenyl)propan-1-one.

Workup

  1. additionare added
  2. customover the course of 1 h
  3. customThe resultant mixture is partitioned between water (30 ml) and dichloromethane (30 ml)
  4. extractionThe resultant aqueous phase is subsequently extracted with dichloromethane (2×30 ml)
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-8910cace6594478ea10165513f8aa352
Source dataset
uspto-grants-2011_03
Patent number
US07906684B2

Reaction notes

Loading…