Oxygen → HCID 14936905, compound

HRID 1647002Notes

Reaction equation

HRID 1647002 reaction equation
[C:1]1([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]=2[OH:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=O>Cl[Cu].C(#N)CCC>[CH3:13][C:12]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:8]([OH:20])[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:11]=1[C:11]1[CH:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]([OH:20])=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:12]=1[CH3:13]

Participants

5

Reactant 2

HCID 977OxygenHCID 14936908HCID 14936908, compound

Product 1

HCID 14936905HCID 14936905, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8008ButyronitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a 250 mL three necked round bottom flask, equipped with a condenser and magnetic stirrer was added 100 g (0.48 mol) of diphenylacetone and 33.3 g (0.48 mol) of acrolein, 50 mL of diethylamine and 10 mL of triethylamine. After reacting for 3 hours at room temperature methanol was added to the reaction mixture and the product crystallized to yield 101 g (85%) of 3-methyl-2,6-diphenyl-2-cyclohexanone, m.p.: 99°-101° C. Dehydrogenation of 80 g (0.32 mol) of this product in the presence of 4 g of 5% palladium on carbon catalyst was carried out for 20 min at 260° C. The reaction mixture was cooled and dissolved in hot ethanol and filtered to yield 65.1 g (83%) of 2,6-diphenyl-3-methylphenol. 50 g of 2,6-diphenyl-3-methylphenol was treated with 3.8 g of CuCl and 400 mL of butyronitrile. The reaction was heated to 100° C. while passing oxygen through for 4 hours. A while solid precipitated during the reaction.

Workup

  1. customthrough for 4 hours
  2. customA while solid precipitated during the reaction

Sources & evidence

ORD record
ord-831b73fe17ae46888a2c6b6b2b25d34a
Source dataset
uspto-grants-1993_01
Patent number
US05182358

Reaction notes

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