Phosphinic Acid → Biphenyl

Participants

Reaction Steps

Hydriodic acid (10 ml) and hypophosphorous acid (1 ml) were heated and stirred at ca. 100° while 1.024 g of 2-biphenyl-carboxaldehyde diethyl acetal (m.p. 63°, obtained from 2-biphenyl-magnesium iodide and ethyl orthoformate, biphenyl being removed from the crude product by draining in tile then steam-distillation. Anal. Calc. for C17H20O2 : C, 79.65; H, 7.86. Found: C, 79.48; H, 7.84) in 5 ml of acetic acid was added. The mixture was stirred and slowly distilled under the vapour reached 125° after 1 hr. The combined distillate and residue were diluted with water and the product isolated using ether. It was sublimed at <100° (5 × 10-4 mm) and crystallized from methanol as colourless prisms (83%, m.p. 117.5°-118°, mixed m.p. with authentic fluorene of m.p. 118°-119°:117.5°-119°). Anal. Calcd. for C13H10 : C, 93.94; H, 6.06. Found: C, 93.67; H, 6.20.

Provenance & Evidence