M-Cresol → HCID 168648, compound

HRID 1600509Notes

Reaction equation

HRID 1600509 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[CH:9]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16].[CH2:17]=[O:18]>O.O.C(O)(=O)C(O)=O.O>[CH:5]1[C:6]([OH:7])=[CH:1][CH:2]=[C:3]([CH3:8])[CH:4]=1.[CH:9]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16].[CH2:17]=[O:18]

Participants

6

Reactant 3

HCID 342M-CresolHCID 712FormaldehydeHCID 2879P-Cresol

Product 1

HCID 168648HCID 168648, compound

Reagents, catalysts & solvents 2

HCID 61373Oxalic acid dihydrateCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixed solution of 60.0 g (0.55 mol) of p-cresol, 60.0 g (0.55 mol) of m-cresol and 2.4 g of oxalic acid dihydrate was added dropwise 33.7 g (0.42 mol) of a 37% formaldehyde solution with stirring at 100° C., and the mixture was reacted with stirring at 100±50° C. for 4 hours. After the end of the reaction, 2,000 ml of water was poured into the reaction solution to cause precipitation. After removing the supernatant by decantation, the precipitate was dissolved in 120 ml of acetone and 1,200 ml of water was poured into the solution to cause precipitation. After the supernatant has been decanted, the solution was evaporated to dryness under reduced pressure to give 74.5 g of residual p-cresol/m-cresol/formaldehyde polycondensate as faintly yellow-tinted waxy crystals. Mw≈880; Mw/Mn=2.07 (GPC with polystyrene calibration).

Workup

  1. customthe mixture was reacted
  2. stirringwith stirring at 100±50° C. for 4 hours
  3. additionwas poured into the reaction solution
  4. customprecipitation
  5. customAfter removing the supernatant by decantation
  6. dissolutionthe precipitate was dissolved in 120 ml of acetone
  7. addition1,200 ml of water was poured into the solution
  8. customprecipitation
  9. customAfter the supernatant has been decanted
  10. customthe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-05d848cc7e4b4d96811e6138d437ff2d
Source dataset
uspto-grants-1999_11
Patent number
US05976759

Reaction notes

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