Potassium Carbonate → ({4-[Cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)acetonitrile

HRID 229279Notes

Reaction equation

HRID 229279 reaction equation
[C:1]1(=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]#[N:32]>CC(C)=O>[C:1]1(=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:30][C:31]#[N:32])=[CH:18][CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 115874204,4'-(Cycloheptylidenemethylene)diphenol

Product 1

HCID 11209805({4-[Cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)acetonitrileYield 13.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The O-alkylation procedure described for 190 was followed. To stirred mixture of 4,4′-(cycloheptylidenemethanediyl)diphenol (189) (1.18 g, 4 mmol), K2CO3 (0.691 g, 5 mmol) and acetone (50 mL) was added bromoacetonitrile (0.418 mL, 6.0 mmol). The reaction mixture was refluxed for 3.5 h. Standard work-up and purification by silica gel chromatography afforded 0.175 g (13%) of compound 216 as a white solid and 0.700 g (47%) of the bis-alkylated material 2,2′-[(cycloheptylidenemethanediyl)bis(benzene-4,1-diyloxy)]diacetonitrile as a white solid. IR (film): 3413, 2921, 1605, 1504,1210, 1170, 828, 729 cm−1. 1H NMR (300 MHz, CDCl3): δ 7.14 (d, J=8.4 Hz, 2H), 7.02 (d, J=8.4 Hz, 2H), 6.91 (d, J=8.4 Hz, 2H), 6.76 (d, J=8.1 Hz, 2H), 5.0 (br, 1H), 4.74 (s, 2H), 2.33 (br s, 4H), 1.60 (s, 8H). LCMS (ESI): m/z 332 (M−H)−. Anal. Calcd for C22H23NO2, C, 79.25; H, 6.95; N, 4.20; Found: C, 79.14, H, 6.90, N, 4.21.

Workup

  1. temperatureThe reaction mixture was refluxed for 3.5 h
  2. customStandard work-up and purification by silica gel chromatography

Sources & evidence

ORD record
ord-b73ec822008f42df82c54522bf5cd481
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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