Hydrochloric Acid → Methanone, [1,1'-biphenyl]-4-yl(3-methoxyphenyl)-

Participants

Reaction Steps

In an oven-dried flask placed under a nitrogen atmosphere, 3-anisoyl chloride (195 g) and biphenyl (190 g) were stirred in dichloromethane (1.4 L). The flask was placed in an ice bath and to it was added anhydrous aluminum chloride (172 g) in portions, each spaced 10 minutes apart. After the aluminum chloride addition was complete the reaction mixture was heated to reflux for 2 hours. After cooling to room temperature, the reaction mixture was slowly poured into a beaker containing a 10% aqueous solution of hydrochloric acid (1.5 L) and ice while stirring vigorously. A separatory funnel was used to separate the organic and aqueous layers. The recovered organic layer was then washed with deionized water three times with 1 liter each time, hereinafter designated as (3×1 L), dried over sodium sulfate and concentrated by rotary evaporation. Crystals formed while sitting overnight and were collected by vacuum filtration. A recrystallization was then performed by dissolving the crystals in a solution of 10% methanol/90% dichloromethane and subsequently removing nearly all of the solvent by rotary evaporation. Crystals formed while sitting overnight and were collected by vacuum filtration yielding 153 g of [1,1′-biphenyl]-4-yl(3-methoxyphenyl)methanone.

Provenance & Evidence