4'-Methoxyacetophenone → HCID 24815140, compound

Participants

Reaction Steps

4.0 ml of LDA 1M in THF (4.0 mmol) are added under nitrogen to a solution of p-methoxyacetophenone (500 mg, 3.3 mmol) in THF (tetrahydrofuran) (15 ml) at −78° C. The mixture is stirred for 1 h before 5 ml of a THF solution of p-tert-butylbenzaldehyde (594 mg, 3.7 mmol) are added. The reaction is allowed to reach −40° C. 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-tert-butylphenyl)-3-hydroxy-1-(4-methoxyphenyl)propan-1-one.

Provenance & Evidence