O-Cresol → O-Cresol

HRID 885522Notes

Reaction equation

HRID 885522 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:11](Br)[CH:12]=[CH2:13]>CN(C=O)C>[CH2:13]([O:7][CH2:6][CH:1]=[CH2:8])[CH:12]=[CH2:11].[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 335O-CresolHCID 7841Allyl bromideHCID 24758Sodium hydride

Product 2

HCID 335O-CresolHCID 11194Diallyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An o-cresol novolac resin (9.8 g, 0.082 mol) and DMF (70 mL) are added under nitrogen to a 250 ml 3-neck flask. NaH (2.55 g, 0.106 mol) is slowly added to the stirred solution. Allyl bromide (14.9 g, 0.123 mol) is then added drop-wise over 30 minutes. The reaction is continued for 19 hours at room temperature. The solids are filtered off and 70 mL toluene is added. The resulting solution is washed with 70 mL of water. The product allyl ether of the o-cresol novolac resin is isolated by evaporating off toluene, then drying overnight in vacuum oven at 60° C.

Workup

  1. filtrationThe solids are filtered off
  2. addition70 mL toluene is added
  3. washThe resulting solution is washed with 70 mL of water

Sources & evidence

ORD record
ord-00c52f114ffa4eaa88afde4467492a68
Source dataset
uspto-grants-2012_08
Patent number
US08242183B2

Reaction notes

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