Hydrochloric Acid → (1,1'-Biphenyl)-4-carbonitrile

HRID 21910Notes

Reaction equation

HRID 21910 reaction equation
O[C@@]1(C)C=C[C@H]2[C@H]3[C@H]([C@@H]([C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=5)=[CH:22][CH:21]=4)C[C@]12C)[C@@H]1C(=CC(=O)CC1)CC3.Cl.CCCCCC.C(OCC)(=O)C>CC(C)=O>[C:26]1([C:23]2[CH:22]=[CH:21][CH:20]=[CH:25][CH:24]=2)[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 676862154'-[17beta-Hydroxy-17alpha-methyl-3-oxo-oestra-4,15-dien-11beta-yl][1,1'-biphenyl]-4-carbonitrile

Product 1

HCID 18021(1,1'-Biphenyl)-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

260 mg of 4'-[3,3-[1,2-ethanediylbis(oxy)]-17β-methoxy-17α-methyloestra-5,15-dien-11β-yl][1,1'-biphenyl]-4-carbonitrile are reacted with 0.7 ml of 4 normal aqueous hydrochloric acid in 14 ml of acetone in the manner described in Example 1 r). Column chromatography on silica gel with a mixture of hexane/ethyl acetate yields 218 mg of 4'-17β-methoxy-17α-methyl-3-oxo-oestra-4,15-dien-11β-yl][1,1'-biphenyl]-4-carbonitrile in the form of a white foam.

Sources & evidence

ORD record
ord-2c9353d9d1a145118a5403d56857deda
Source dataset
uspto-grants-1995_06
Patent number
US05426102

Reaction notes

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