4-Hydroxybenzophenone → 4-[Phenyl(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

HRID 2241048Notes

Reaction equation

HRID 2241048 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.[CH3:16][C:17]1([CH3:26])[CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19](=O)[CH2:18]1>[Zn].Cl[Ti](Cl)(Cl)Cl.C1COCC1>[C:10]1([C:8](=[C:19]2[CH2:20][C:21]([CH3:24])([CH3:23])[CH2:22][C:17]([CH3:26])([CH3:16])[CH2:18]2)[C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 143474-HydroxybenzophenoneHCID 843993,3,5,5-Tetramethylcyclohexanone

Product 1

HCID 685023444-[Phenyl(3,3,5,5-tetramethylcyclohexylidene)methyl]phenolYield 94.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The McMurry procedure described for 9 (example 5, step 1) was utilized using (4-hydroxyphenyl)(phenyl)methanone (2.97 g, 14.9 mmol), 3,3,5,5-tetramethylcyclohexanone (6.25 g, 44.9 mmol), Zn (9.69 g, 149 mmol), TiCl4.2THF complex (25 g, 7.5 mmol), and THF (200 mL). Standard work-up followed by purification gave 4.50 g (91%) of the title product 32 as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 7.04 (d, J=8.4 Hz, 2H), 6.74 (d, J=8.4 Hz, 2H), 1.98 (s, 2H), 1.95 (s, 2H), 1.28 (s, 2H), 0.93 (s, 6H), 0.92 (s, 6H).

Workup

  1. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-5c2b47f98ba842be81ad93c73cca7118
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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