P-Cymene → HCID 10308021, compound

HRID 895168Notes

Reaction equation

HRID 895168 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12][CH2:11]3)=[CH:4][CH:3]=1.CC1C=CC(C(C)C)=CC=1>[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([OH:18])=[CH:13][CH:12]=[CH:11]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7463P-CymeneHCID 11436350HCID 11436350, compound

Product 1

HCID 10308021HCID 10308021, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a 25 mL flask was added 6-(4-hydroxyphenyl)-1-tetralone (500 mg, 2.12 mmol), palladium on carbon (510 mg) and p-cymene (15 mL). The mixture was heated to reflux for 24 h, cooled, filtered through celite and extracted with 1 M NaOH (2×25 mL). The aqueous layer was then acidified, extracted with ether (3×), and passed through a silica plug. Concentration under reduced pressure afforded 260 mg (53%) product as a brown solid: mp above 200° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 6.82 (1H, d, J=7.5 Hz), 6.87 (2H, d, J=8.1 Hz), 7.29 (1H, t, J=7.5 Hz), 7.38 (1H, d, J=7.5 Hz), 7.63 (2H, d, J=8.2 Hz), 7.70 (1H, d, J=8.5 Hz), 7.99 (1H, s) 8.14 (1H, d, J=8.5 Hz), 9.59 (1H, s), 10.09 (1H, s); MS m/z 235 (M−H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. temperaturecooled
  4. filtrationfiltered through celite
  5. extractionextracted with 1 M NaOH (2×25 mL)
  6. extractionextracted with ether (3×)
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-7176a9d16ae64b41a22c345928c098ec
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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