Methacrylic Acid → 11-Bromoundecyl methacrylate

HRID 2308112Notes

Reaction equation

HRID 2308112 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 at 0° C. over a period of 45 minutes. The reaction mixture was allowed to warm to room temperature, stirred for 19 hours and filtered. The filtrate was concentrated by evaporation. The residue was purified by chromatography using a silica gel column (170 g) and toluene as eluant to give 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
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-ea0edd11bfde48fc86d381479c5dd8ca
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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