Ethyl vinyl ether → 1-(1'-Ethoxyethoxy)-3-methacryloyloxyadamantane

HRID 563449Notes

Reaction equation

HRID 563449 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([O:12][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:18]([O:20][CH:21]=[CH2:22])[CH3:19].C([O-])([O-])=O.[Na+].[Na+]>O1CCCC1.Cl>[CH2:18]([O:20][CH:21]([O:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([O:12][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])([CH2:5]3)[CH2:3]1)[CH2:9]2)[CH3:22])[CH3:19]

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 10340Sodium CarbonateHCID 118565233-Hydroxy-1-methacryloyloxyadamantane

Product 1

HCID 579149951-(1'-Ethoxyethoxy)-3-methacryloyloxyadamantaneYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 23.6 g (0.1 mols) of 1-hydroxy-3-methacryloyloxyadamantane (HAMA) was dissolved in 100 ml of tetrahydrofuran (THF) and 21.6 g (0.3 mols) of vinyl ethyl ether and 0.1 ml (1 mmol) of hydrochloric acid were added, followed by stirring at room temperature for 3 days. The reaction solution was neutralized with an aqueous Na2CO3 solution added and, after phase separation, the upper layer was washed with water so as to adjust the pH to 7. MgSO4 was added and the solution was dehydrated and filtered, and then concentrated to dryness to obtain 30 g of 1-(1′-ethoxyethoxy)-3-methacryloyloxyadamantane (EEAM) (yield: 99%)

Workup

  1. additionadded
  2. customafter phase separation
  3. washthe upper layer was washed with water so as
  4. additionMgSO4 was added
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b16c97d351ee49668f703146f841eec4
Source dataset
uspto-grants-2011_11
Patent number
US08067515B2

Reaction notes

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