Methyl 4-(4-hydroxybenzoyl)benzoate → methyl 4-[(4-hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]benzoate

HRID 229207Notes

Reaction equation

HRID 229207 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.[CH3:20][C:21]1([CH3:30])[CH2:26][C:25](=O)[CH2:24][C:23]([CH3:29])([CH3:28])[O:22]1>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:25]2[CH2:24][C:23]([CH3:29])([CH3:28])[O:22][C:21]([CH3:30])([CH3:20])[CH2:26]2)[C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10038024Methyl 4-(4-hydroxybenzoyl)benzoate2×HCID 118296912,2,6,6-Tetramethyloxan-4-one

Product 1

HCID 68654824methyl 4-[(4-hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]benzoateYield 93%

Procedure

The general McMurry protocol, described for 14 was followed. Thus, methyl 4-[(4-hydroxyphenyl)carbonyl]benzoate (24 (0.196 g, 0.765 mmol) and 2,2,6,6-tetramethyltetrahydro-4H-pyran-4-one (52) (0.370 g, 2.37 mmol) were subjected for McMurry coupling reaction conditions. Standard work-up followed by purification by column chromatography gave 0.272 g (93%) of the title compound 101 as a white foam. 1H NMR (300 MHz, CDCl3): δ 7.98 (d, J=8.1 Hz, 2H), 7.26 (d, J=8.7 Hz, 2H), 7.05 (d, J=8.7 Hz, 2H), 6.78 (d, J=8.4 Hz, 2H), 3.92 (s, 3H), 2.27 (s, 2H), 2.21 (s, 2H), 1.28 (s, 6H), 1.25 (s, 6H). LCMS (ESI): m/z 379 (M−H)−.

Workup

  1. customStandard work-up followed by purification by column chromatography

Sources & evidence

ORD record
ord-6205e12269cc4d93ae5562bb650d7cdf
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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