Acetone → HCID 67686069, compound

HRID 1600514Notes

Reaction equation

HRID 1600514 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9]1([CH2:17][OH:18])[C:10](CO)=[CH:11][CH:12]=[CH:13][CH:14]=1.C[C:20](C)=[O:21]>CS(O)(=O)=O.O>[CH:5]1[C:6]([OH:7])=[CH:1][CH:2]=[C:3]([CH3:8])[CH:4]=1.[OH:18][CH2:17][C:9]1[CH:14]=[CH:13][C:12]([CH2:20][OH:21])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 2879P-CresolHCID 691531,2-Benzenedimethanol

Product 1

HCID 67686069HCID 67686069, compound

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

38.4 g (0.36 mol) of p-cresol and 35.0 g (0.25 mol) of xylene-α,α'-diol were dissolved under heating, then 0.15 g of methanesulfonic acid was added thereto at 90-100° C. and the mixture was stirred and reacted at the same temperature for 2 hours. After cooling, 100 ml of acetone was poured into and dissolved in the reaction solution and then the solution was poured into 2,000 ml of water, stirred and then allowed to stand, after which the supernatant was decanted and the residue was dissolved in 100 ml of acetone, poured into 2,000 ml of water and stirred. The solution was allowed to stand, the supernatant was decanted and the residue was evaporated to dryness under reduced pressure to give 65.0 g of p-cresol/1,4-dihydroxymethylbenzene polycondensate as faintly yellow-tinted powdery crystals. Mw≈6,700; Mw/Mn=3.50 (GPC with polystyrene calibration).

Workup

  1. temperatureunder heating
  2. customreacted at the same temperature for 2 hours
  3. temperatureAfter cooling
  4. dissolutiondissolved in the reaction solution
  5. stirringstirred
  6. customafter which the supernatant was decanted
  7. dissolutionthe residue was dissolved in 100 ml of acetone
  8. additionpoured into 2,000 ml of water
  9. stirringstirred
  10. customthe supernatant was decanted
  11. customthe residue was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-23ef266077a64b2b850810f79d67f88e
Source dataset
uspto-grants-1999_11
Patent number
US05976759

Reaction notes

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