Methacrylic Acid → HCID 86718245, compound

HRID 2402483Notes

Reaction equation

HRID 2402483 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[N+:2]=[N-:3].[C:11](O)(=[O:15])[C:12]([CH3:14])=[CH2:13].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])(=[O:15])[C:12]([CH3:14])=[CH2:13]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 110517786-Azidohexan-1-ol

Product 1

HCID 86718245HCID 86718245, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 500 mL round bottom flask, a solution of 1-azido-6-hydroxyhexane (14.3 g, 100 mmol), methacrylic acid (7.74 g, 90 mmol), and 4-dimethylaminopyridine (DMAP) (3.67 g, 30 mmol) in 100 mL of methylene chloride was cooled to 0° C. Dicyclohexylcarbodiimide (DCC) (20.63 g, 100 mmol) was dissolved in 50 mL methylene chloride and added slowly to the solution. The resulting mixture was warmed to room temperature and stirred overnight. The precipitate was removed by filtration. After removal of the solvent and silica gel column chromatography (10:1 mixture of hexane and ethyl acetate), the product was obtained as a colorless liquid (yield: 16.1 g, 85%).

Workup

  1. additionadded slowly to the solution
  2. customThe precipitate was removed by filtration
  3. customAfter removal of the solvent and silica gel column chromatography (10:1 mixture of hexane and ethyl acetate)

Sources & evidence

ORD record
ord-e296128ece38404ea80b0b82bfafb549
Source dataset
uspto-grants-2014_08
Patent number
US08796372B2

Reaction notes

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