M-Cresol → HCID 86588494, compound

HRID 2306528Notes

Reaction equation

HRID 2306528 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[C:9]1([OH:17])[C:10]([CH3:16])=[CH:11][CH:12]=[C:13]([CH3:15])[CH:14]=1.O.O.C(O)(=O)C(O)=O.C=O>C(C(C)=O)C(C)C.C(OC(C)COC)(=O)C.CCCCCCC.C(O)(=O)C>[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[C:9]1([OH:17])[C:10]([CH3:16])=[CH:11][CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

9

Reactant 4

HCID 342M-CresolHCID 712FormaldehydeHCID 72672,5-DimethylphenolHCID 61373Oxalic acid dihydrate

Product 1

HCID 86588494HCID 86588494, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 7909Methyl Isobutyl KetoneSolvent3×HCID 7946Propylene glycol methyl ether acetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 1 L four-necked flask equipped with a reflux tube, stirring apparatus and thermometer were charged 150.4 g of m-cresol, 67.9g of 2,5-xylenol, 10.0 g of oxalic acid dihydrate, 66.3 g of 90% acetic acid and 218 g of methyl isobutyl ketone and the mixture was heated up to 80° C. Into this was dropped 142.2 g of a 37% formaldehyde aqueous solution over 1 hour. Thereafter, the mixture was heated up to reflux temperature and kept at the same temperature for 12 hours. The resulted reaction solution was diluted with methyl isobutyl ketone, and washed with water and dehydrated, to obtain a 38.0% methyl isobutyl ketone solution of a novolak resin. 644 g of this resin solution was charged into a 5 L bottom-discharging type flask, diluted with 411 g of methyl isobutyl ketone. Thereto, 715 g of n-heptane was charged and the mixture was stirred at 60° C. and allowed to stand still, then, separated to obtain a novolak resin solution in the lower layer. This novolak resin solution was diluted with propylene glycol methyl ether acetate and then concentrated, to obtain a propylene glycol methyl ether acetate solution of a novolak resin. This resin is called resin A7.

Workup

  1. customInto a 1 L four-necked flask equipped with a reflux tube
  2. temperatureThereafter, the mixture was heated up
  3. temperatureto reflux temperature
  4. customThe resulted reaction solution
  5. washwashed with water
  6. customto obtain a 38.0% methyl isobutyl ketone solution of a novolak resin
  7. stirringthe mixture was stirred at 60° C.
  8. customseparated
  9. customto obtain a novolak resin solution in the lower layer
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-26e777b09ace4b758b24a75e323cee67
Source dataset
uspto-grants-2004_12
Patent number
US06828079B2

Reaction notes

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