P-Cresol → 2-Cumyl-4-methylphenol

HRID 1062519Notes

Reaction equation

HRID 1062519 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 44.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a 200 ml reactor thoroughly dried and purged with nitrogen, 34.15 g (316.0 mmol) of paracresol, 2.50 g of Umberist-15E (trade name, available from Organo Co.) and 20 ml of toluene were introduced. To the reactor, a solution containing 14.40 g (105.0 mmol) of 4-cumylphenol diluted with 30 ml of a toluene was dropwise added at 80° C., followed by stirring for 17 hours. After the system was cooled to room temperature, the reaction solution was filtered with washing with hexane. The resulting liquid was purified by silica gel column chromatography to obtain 10.52 g (yield: 44%) of 2-cumyl-4-methylphenol.

Workup

  1. customInto a 200 ml reactor thoroughly dried
  2. additionwere introduced
  3. additionwas dropwise added at 80° C.
  4. filtrationthe reaction solution was filtered
  5. washwith washing with hexane
  6. customThe resulting liquid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-42b90309070b4f4794a9ea4161bcfd79
Source dataset
uspto-grants-2005_11
Patent number
US06962890B2

Reaction notes

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