(4-Bromophenyl)(4-hydroxyphenyl)methanone → 4-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenol

HRID 229166Notes

Reaction equation

HRID 229166 reaction equation
BrC1C=CC(C(=C2CCOCC2)C2C=CC(O)=CC=2)=CC=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=O)=[CH:25][CH:24]=1.[CH3:38][C:39]1([CH3:48])[CH2:44][C:43](=O)[CH2:42][C:41]([CH3:47])([CH3:46])[O:40]1>[Zn].Cl[Ti](Cl)(Cl)Cl>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[C:43]2[CH2:42][C:41]([CH3:47])([CH3:46])[O:40][C:39]([CH3:48])([CH3:38])[CH2:44]2)[C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 4570728(4-Bromophenyl)(4-hydroxyphenyl)methanoneHCID 118296912,2,6,6-Tetramethyloxan-4-oneHCID 686541974-[(4-Bromophenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenol

Product 1

HCID 686543254-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenolYield 76%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalyst

Procedure

Following the procedure described for compound 46, zinc powder (0.957 g, 14.6 mmole), TiCl4 (0.800 mL, 7.30 mmole), (4-bromophenyl)(4-hydroxyphenyl)methanone (2) (0.512 g, 1.85 mmole) and 2,2,6,6-tetramethyltetrahydro-4H-pyran-4-one (52) (0.851 mL, 5.45 mmole), afforded 0.564 g (76%) of 53 as a white foamy solid. 1H NMR (CDCl3): δ 7.41 (d, J=8.3 Hz, 2H), 7.02 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.4 Hz, 2H), 6.76 (d, J=8.3 Hz, 2H), 4.99 (s, 1H), 2.24 (s, 2H), 2.20 (s, 2H), 1.22 (s, 6H), 1.21 (s, 6H).

Sources & evidence

ORD record
ord-3676bf1076144ab080b4fe3cc1bd7d5e
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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