O-Cresol → 4-Nonyl-o-cresol

HRID 987360Notes

Reaction equation

HRID 987360 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][CH2:10][CH2:11][CH2:12][CH:13]([CH:15]([CH3:17])C)C.[CH3:18][CH2:19]CC(CC(C)C)C.CC(CC(C(C)C)C)C>>[CH2:18]([C:3]1[CH:2]=[C:1]([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=1)[CH2:19][CH2:17][CH2:15][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

Participants

3

Reactant 2

HCID 335O-CresolHCID 2637413987-01-4

Product 1

HCID 844264-Nonyl-o-cresolYield 253.9%

Procedure

o-Cresol (108 g, 1 mol), tripropylene (131.74 g), and Amberlyst 15 (8.55 g) were stirred for 20 h at 75° C. and 2 h at 90° C. At ambient temperature the reaction mixture was mixed with heptanes and filtered to remove the catalyst. Removal of the solvent in vacuo gave crude product (225.23 g), which was distilled to obtain pure 4-nonyl-2-cresol (203.76 g) in 87% yield.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. customRemoval of the solvent in vacuo
  4. customgave crude product (225.23 g), which
  5. distillationwas distilled

Sources & evidence

ORD record
ord-992b3c801f0f4d87a8fd8cce6653588e
Source dataset
uspto-grants-2003_10
Patent number
US06632410B2

Reaction notes

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