P-Cresol → 2-Cumyl-4-methylphenol

HRID 229614Notes

Reaction equation

HRID 229614 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9](C1C=CC(O)=CC=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH3:10]>C1(C)C=CC=CC=1>[C:9]([C:1]1[CH:2]=[C:3]([CH3:8])[CH:4]=[CH:5][C:6]=1[OH:7])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 2879P-CresolHCID 117424-Cumylphenol

Product 1

HCID 948562-Cumyl-4-methylphenolYield 44.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Paracresol 34.15 g (316.0 mmol), Amberlyst 15E 2.50 g, and toluene 20 ml were charged in a sufficiently dried 200 ml reactor purged with argon, 30 ml of a toluene solution containing 4-cumylphenol 14.40 g (105.5 mmol) was added dropwise to the reactor at 80° C. and then the resultant mixture was stirred for 17 hours. After cooling to a room temperature, the resultant mixture was filtered while being washed with hexane. The obtained liquid was purified by silica gel column chromatography to obtain 2-cumyl-4-methylphenol 10.52 g (44%).

Workup

  1. custompurged with argon, 30 ml of a toluene solution
  2. additionwas added dropwise to the reactor at 80° C.
  3. filtrationthe resultant mixture was filtered
  4. washwhile being washed with hexane
  5. customThe obtained liquid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b5193aa79351401fb8212dea167df62d
Source dataset
uspto-grants-2009_07
Patent number
US07563849B2

Reaction notes

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