Phosphinic Acid → Biphenyl

HRID 1834438Notes

Reaction equation

HRID 1834438 reaction equation
[PH2](O)=[O:2].C([O:6][CH:7]([O:20][CH2:21][CH3:22])[C:8]1[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)C>I>[CH:7]([O-:2])([O-:6])[O:20][CH2:21][CH3:22].[C:9]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]=1

Participants

5

Reactant 2

HCID 4124402Phosphinic AcidHCID 18937494HCID 18937494, compound

Product 2

HCID 7095BiphenylHCID 53630039Ethylorthoformate

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

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.

Sources & evidence

ORD record
ord-a33f37b25b6b418ba8e622cd56ed7365
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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