Isopropanol → 2-Hydroxyethyl Methacrylate

HRID 634339Notes

Reaction equation

HRID 634339 reaction equation
[CH3:1][CH:2](O)[CH3:3].[C:5]([O-:8])(=O)[CH3:6].[K+].[C:10]([O-:13])(O)=[O:11].[Na+]>C(O)C>[CH3:3][C:2]([C:10]([O:13][CH2:6][CH2:5][OH:8])=[O:11])=[CH2:1]

Participants

5

Reactant 3

HCID 3776Isopropanol4×HCID 516892Sodium BicarbonateHCID 517044Potassium Acetate

Product 1

HCID 133602-Hydroxyethyl MethacrylateYield 6,287.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

10.02 g of the intermediate siloxane of formula 5, 15.52 g of ally alcohol (Wako Pure Chemical Industries), 25.04 g of 2-propanol (super dehydrated) (Wako Pure Chemical Industries), 0.20 g of 10% potassium acetate in ethanol, 0.10 g of 1% BHT/IPA, and 0.05 g of 1% MQ/IPA were added into 300 ml eggplant-shaped flask. To this solution 0.40 g of 1% H2PtCl6/6H20/IPA was added and stirred at 50° C. for 13.5 h. After that 0.4128 g of 1% NaHCO3 aq. was added and stirred for over 1 h at room temperature. Then the reaction mixture was evaporated and vacuum dried at 35° C. To this mixture about 5 g of acetone and 15 g of DI water were added with vigorous shaking. The mixture was then centrifuged (7000 rpm, 5° C., 10 min). The upper (aqueous) layer was removed. This operation was repeated three times in total. To this mixture 5 g IPA was added and the reaction mixture was evaporated and vacuum-dried at 40° C. Then 0.06 g of 1% BHT/IPA and 0.03 g of 1% MQ/IPA were added and then evaporated and vacuum-dried at 45° C. The reaction yielded 16.6762 g of a polysiloxane, designated H30AA-5K, having the structure of Formula 3 (above) wherein R2 is a methyl group, m is 0, n is ˜30, and p is 0. The siloxane had an HLB value of about 3 and a hydroxyl content of about 13 wt. %.

Workup

  1. stirringstirred for over 1 h at room temperature
  2. customThen the reaction mixture was evaporated
  3. customvacuum dried at 35° C
  4. additionTo this mixture about 5 g of acetone and 15 g of DI water were added with vigorous shaking
  5. custom(7000 rpm, 5° C., 10 min)
  6. customThe upper (aqueous) layer was removed
  7. additionTo this mixture 5 g IPA was added
  8. customthe reaction mixture was evaporated
  9. customvacuum-dried at 40° C
  10. additionThen 0.06 g of 1% BHT/IPA and 0.03 g of 1% MQ/IPA were added
  11. customevaporated
  12. customvacuum-dried at 45° C

Sources & evidence

ORD record
ord-03f92d41182b44b9b4be062eb10b9dcc
Source dataset
uspto-grants-2016_04
Patent number
US09322959B2

Reaction notes

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