Water → 4-Methoxyphenol

HRID 358947Notes

Reaction equation

HRID 358947 reaction equation
[C:1](O)(=[O:4])C=C.OS(O)(=O)=O.[OH2:11].[C:12]1(C)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Cu-]=O>[CH3:1][O:4][C:12]1[CH:17]=[CH:16][C:15]([OH:11])=[CH:14][CH:13]=1

Participants

6

Procedure

A mixture of 40 g of the above propoxylated pentaerythritol, 30.2 g acrylic acid, 0.4 g of copper (I) oxide and 1.2 cm3 conc. H2SO4 in toluene (150 cm3) was heated with stirring in the presence of a Dean and Stark trap. The reaction was allowed to continue until 6.1 cm3 of water had been liberated. The mixture was then cooled and washed with 20% w/v aqueous sodium chloride (2×50 cm3 aliquots), then with 15% w/v aqueous potassium bicarbonate (2×100 cm3 aliquots) and finally a further wash with 20% w/v aqueous sodium chloride (2×50 cm3 aliquots). The resulting solution was then filtered and dried over anhydrous sodium sulphate. The solvent was then removed leaving the polyacrylate product as a colourless oil to which 0.2% w/w of 4-methoxyphenol, a polymerisation inhibitor, was then added.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was then cooled
  3. washwashed with 20% w/v aqueous sodium chloride (2×50 cm3 aliquots)
  4. washwith 15% w/v aqueous potassium bicarbonate (2×100 cm3 aliquots) and finally a further wash with 20% w/v aqueous sodium chloride (2×50 cm3 aliquots)
  5. filtrationThe resulting solution was then filtered
  6. dry with materialdried over anhydrous sodium sulphate
  7. customThe solvent was then removed

Sources & evidence

ORD record
ord-c132eba332844ca7940894346ac10cd3
Source dataset
uspto-grants-1991_03
Patent number
US04999271

Reaction notes

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