[1,1';3',1'']Terphenyl-2'-yl-acetonitrile → 1,1':3',1''-Terphenyl-2'-ylacetic acid

HRID 1181852Notes

Reaction equation

HRID 1181852 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2CC#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([OH:25])(=[O:24])[CH3:23].S(=O)(=O)(O)O.O>O>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:8]=2[CH2:23][C:22]([OH:25])=[O:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 69422715[1,1';3',1'']Terphenyl-2'-yl-acetonitrileHCID 86597087Acetic acid sulfuric acid water

Product 1

HCID 694229871,1':3',1''-Terphenyl-2'-ylacetic acidYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [1,1′;3′,1″]terphenyl-2′-yl-acetonitrile (0.78 g, 2.9 mmol) in 28 mL of 10:3:1 acetic acid/sulfuric acid/water was refluxed for 2 days The reaction mixture was cooled and diluted with water. The aqueous was extracted with diethyl ether, dried over magnesium sulfate and concentrated to give 1,1′:3′,1″-terphenyl-2′-ylacetic acid as a tan solid (0.64 g, 76%): MS (ESI) m/z 287.1 (M−H); MS (ESI) m/z 575.2 (2M−H); MS (ESI) m/z 333 (M+FA−H); HRMS calcd for C20H16O2, 288.1150. Found (ESI+), 289.12244; 1H NMR (DMSO-d6): δ 3.30 (s, 2H), 7.30-7.50 (m, 13H), 12.07 (br s, 1H); Anal. Calcd for C20H16O2: C, 83.31; H, 5.59. Found: C, 83.02; H, 5.35.

Workup

  1. temperaturewas refluxed for 2 days The reaction mixture
  2. temperaturewas cooled
  3. extractionThe aqueous was extracted with diethyl ether
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6110d6df4e084259992782bd88d6e221
Source dataset
uspto-grants-2007_10
Patent number
US07285682B2

Reaction notes

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