Water → 4'-Pentyl-bicyclohexyl-4-carboxylic acid 3-(2-methyl-acryloyloxy)-propyl ester

HRID 386326Notes

Reaction equation

HRID 386326 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][O:13][C:14]([CH:16]1[CH2:21][CH2:20][CH:19]([CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:24][CH2:23]2)[CH2:18][CH2:17]1)=[O:15].O>CN(C)C=O>[CH3:3][C:2](=[CH2:4])[C:1]([O:6][CH2:10][CH2:11][CH2:12][O:13][C:14]([CH:16]1[CH2:21][CH2:20][CH:19]([CH:22]2[CH2:23][CH2:24][CH:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:26][CH2:27]2)[CH2:18][CH2:17]1)=[O:15])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 4093Methacrylic AcidHCID 24758Sodium hydrideHCID 59289083HCID 59289083, compound

Product 1

HCID 592890824'-Pentyl-bicyclohexyl-4-carboxylic acid 3-(2-methyl-acryloyloxy)-propyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of methacrylic acid (3.5 g, 40.7 mmol) in dimethylformamide (100 ml) is added dropwise to an ice cooled slurry of sodium hydride (60% suspension in paraffin oil) (1.6 g, 40.0 mmol) in dimethylformamide (100 ml). Once addition is complete, the mixture is allowed to warm to room temperature and is stirred for 1 h, the intermediate 4′-pentyl-bicyclohexyl-4-carboxylic acid 3-bromo-propyl ester (15.0 g, 37.4 mmol) in dimethylformamide (100 ml) is added dropwise. The mixture is stirred at 50° C. overnight. The mixture is cooled to room temperature, poured into icy water, and this is extracted three times with DCM. The DCM solution is washed with brine, water and then dried over sodium sulphate. The solution is evaporated to dryness and recrystallised from industrial methylated spirits to afford a white crystalline solid.

Workup

  1. additionOnce addition
  2. stirringThe mixture is stirred at 50° C. overnight
  3. temperatureThe mixture is cooled to room temperature
  4. extractionthis is extracted three times with DCM
  5. washThe DCM solution is washed with brine, water
  6. dry with materialdried over sodium sulphate
  7. customThe solution is evaporated to dryness
  8. customrecrystallised from industrial methylated spirits
  9. customto afford a white crystalline solid

Sources & evidence

ORD record
ord-88a368d43ae244c6a3c511f9e519d674
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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