Triethylamine → Pentadeca-12-ene-1-yl methacrylate

HRID 2182586Notes

Reaction equation

HRID 2182586 reaction equation
[CH2:1]([OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH2:14][CH3:15].[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19].C(N(CC)CC)C>C(Cl)Cl>[C:17]([O:16][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH2:14][CH3:15])(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 13528Methacryloyl chlorideHCID 54287549Pentadeca-12-ene-1-ol2×

Product 1

HCID 54153362Pentadeca-12-ene-1-yl methacrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pentadeca-12-ene-1-ol (22.6 grams) is placed in a three-neck flask under a blanket of nitrogen. The entire reaction contents are cooled in an ice bath. Methacryloyl chloride (10.5 grams) dissolved in about 50 mL of methylene chloride is added slowly to the cooled pentadeca-12-ene-1-ol with vigorous stirring in about 2 hours. Triethylarnine (11.5 g) dissolved in 25 mL of methylene chloride is subsequently added in about an hour. After addition of triethylamine, the solution is allowed to warm to ambient temperature and is stirred for another 4 hours in order to complete the reaction. The precipitated triethylammonium chloride is removed by filtration, and the filtrate is washed with brine solution (saturated NaCl) followed by washings with dil. NaOH and dil. HCl. The organic layer is dried with anhydrous magnesium sulfate and the solvent is removed in vacuo to yield pentadeca-12-ene-1-yl methacrylate in good yields. Pentadeca-12-ene-1-yl methacrylate is stabilized from polymerization by addition of approximately 10 ppm hydroquinone. The structure of the product is verified by 1H and 13C NMR spectroscopy.

Workup

  1. customThe entire reaction contents
  2. temperatureare cooled in an ice bath
  3. additionis subsequently added in about an hour
  4. stirringis stirred for another 4 hours in order
  5. customthe reaction
  6. customThe precipitated triethylammonium chloride is removed by filtration
  7. washthe filtrate is washed with brine solution (saturated NaCl)
  8. washfollowed by washings with dil. NaOH and dil. HCl
  9. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  10. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2695b4f346074c82bac0d04076303e5b
Source dataset
uspto-grants-2005_05
Patent number
US06897255B1

Reaction notes

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