Methyl Isobutyl Ketone → Acrylic Acid

HRID 1712189Notes

Reaction equation

HRID 1712189 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](C23CC4CC(CC(C5C=CC(O[CH2:29][CH:30]6[O:32][CH2:31]6)=CC=5)(C4)C2)C3)=[CH:8][CH:7]=1)C1OC1.CC(CC(C)=[O:38])C>[Br-].C([N+](CC)(CC)CC)C>[C:31]([OH:32])(=[O:38])[CH:30]=[CH2:29].[CH3:1][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:38])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 7909Methyl Isobutyl KetoneHCID 187042671,3-Bis(4-glycidyloxyphenyl)adamantane

Product 2

HCID 6581Acrylic AcidHCID 90154-Methoxyphenol

Reagents, catalysts & solvents 1

HCID 6285Tetraethylammonium BromideCatalyst

Procedure

In a separable flask having an inner volume of 300 ml, equipped with a reflux condenser, a stirrer, a thermometer, and an air inlet were charged 22.4 g of 1,3-bis(4-glycidyloxyphenyl)adamantane obtained by the Synthesis Example 1, 7.6 g of acrylic acid, 20 mL of MIBK, 0.76 g of tetraethylammonium bromide, and 7.6 mg of p-methoxyphenol, and the mixture was heated to 120° C. with flowing a small amount of an air, and stirred for 20 hours. Thereafter, 80 mL of MIBK was added, and the reaction solution was cooled to room temperature. The MIBK solution was washed by 5% by mass of aqueous sodium chloride solution twice, and by pure water once, and then the organic layer was concentrated to obtain 26.8 g of the adamantyl group containing epoxy-modified acrylate having the following formula (purity of 91% by LC).

Workup

  1. customIn a separable flask having
  2. customan inner volume of 300 ml, equipped with a reflux condenser, a stirrer

Sources & evidence

ORD record
ord-381b84799a5c495fb7471b1a09fe3bd0
Source dataset
uspto-grants-2010_09
Patent number
US07790917B2

Reaction notes

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