Methacrylic Acid → 11-Bromoundecyl methacrylate

HRID 479924Notes

Reaction equation

HRID 479924 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[C:14](O)(=[O:18])[C:15]([CH3:17])=[CH2:16].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 7416311-Bromo-1-undecanol

Product 1

HCID 19370211-Bromoundecyl methacrylateYield 98.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

19.2 g (76.4 mmol) 11-bromo-1-undecanol, 7.2 g (84.1 mmol) methacrylic acid and 1.03 g (8.4 mmol) 4-dimethylaminopyridine were dissolved in 157 ml dichloromethane. The solution was subsequently cooled to 0° C. and then a solution of 17.4 g (84.2 mmol) dicyclohexylcarbodiimide in 80 ml dichloromethane was added dropwise, in the course of 45 minutes at 0° C. The reaction was allowed to warm to room temperature, stirred for 19 hours and filtered. The filtrate was concentrated by evaporation. Chromatography of the residue on 170 g silica gel using toluene yielded 19.3 g (98.4%) 2-methylacrylic acid 11-bromoundecyl ester.

Workup

  1. temperatureto warm to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated by evaporation

Sources & evidence

ORD record
ord-b8e8ceee97e741328a7025455a4ece25
Source dataset
uspto-grants-2003_11
Patent number
US06649230B1

Reaction notes

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