3,3,5,5-Tetramethylcyclohexanone → HCID 68654575, compound

HRID 2100175Notes

Reaction equation

HRID 2100175 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=O)=[CH:5][CH:4]=1.[CH3:19][C:20]1([CH3:29])[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22](=O)[CH2:21]1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[C:22]2[CH2:23][C:24]([CH3:27])([CH3:26])[CH2:25][C:20]([CH3:29])([CH3:19])[CH2:21]2)[C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 843993,3,5,5-TetramethylcyclohexanoneHCID 108683214-(4-Methoxybenzoyl)benzonitrile

Product 1

HCID 68654575HCID 68654575, compoundYield 50.2%

Procedure

The general McMurry protocol, described for 14 was used. The reaction was conducted between 4-{[4-(methyloxy)phenyl]carbonyl}benzonitrile (1.00 g, 4.21 mmol) and 3,3,5,5-tetramethylcyclohexanone (1.95 g, 12.64 mmol) to afford 0.760 g (50%) of the title compound 209 as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, J=8.4 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H), 6.85 (d, J=8.7 Hz, 2H), 3.81 (s, 3H), 2.01 (s, 2H), 1.95 (s, 2H), 1.32 (s, 2H), 0.96 (s, 6H), 0.95 (s, 6H).

Sources & evidence

ORD record
ord-e57c37ec0f8e485ab557f90fa2818493
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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