Cyclohexane → 2-Hydroxyethyl Methacrylate

HRID 1354514Notes

Reaction equation

HRID 1354514 reaction equation
[C:1]([O-:14])(=[O:13])[CH2:2][CH2:3]CCCCCCCCC.[C:15]([O-])(=[O:27])[CH2:16]CCCCCCCCCC.[CH2:29]([Sn+2]CCCC)CCC.C1CCCCC1>C1COCC1>[CH3:29][C:2]([C:1]([O:14][CH2:16][CH2:15][OH:27])=[O:13])=[CH2:3]

Participants

4

Conditions

Temperature
40 °C

Procedure

A three-neck reaction flask fitted with a mechanical stirrer, condenser, dropping funnel, and thermometer was charged with 76 parts of a 32.4% THF solution of Polymer D followed by (0.25 parts) of dibutyltin dilaurate (Sigma-Aldrich) and 0.01 parts of BHT. A solution of IEM (4.77 parts) in THF (10 parts) was slowly added from the dropping funnel and the resulting solution heated at 40° C. for 30 minutes. The resulting polymer solution was cooled to room temperature, poured into a large excess of cyclohexane (approximately 5 times volume of reaction mixture), and the precipitated solid collected by filtration and dried in a 30° C. vacuum oven. The dried white solid was designated Example 2 and identified as the polymer of NIPAAM/HEMA with a plurality of the HEMA monomeric units derivatized with IEM to provide monomeric units of the following structure (Me=CH3):

Workup

  1. customA three-neck reaction flask fitted with a mechanical stirrer, condenser
  2. temperatureThe resulting polymer solution was cooled to room temperature
  3. customapproximately 5 times volume of reaction mixture), and the precipitated solid
  4. filtrationcollected by filtration
  5. customdried in a 30° C. vacuum oven
  6. customto provide monomeric units of the following structure (Me=CH3)

Sources & evidence

ORD record
ord-d2638c03a2e84076b1a3c85cba5e6440
Source dataset
uspto-grants-2007_05
Patent number
US07223826B2

Reaction notes

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