Water → HCID 18372053, compound

HRID 884312Notes

Reaction equation

HRID 884312 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C(N(CC)CC)C.[C:15](Cl)(=[O:19])[C:16]([CH3:18])=[CH2:17].O>C(Cl)Cl>[C:15]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6])(=[O:19])[C:16]([CH3:18])=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 699635-Hexen-1-ol

Product 1

HCID 18372053HCID 18372053, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Hexen-1-ol (5.0 g; 50.0 mmol) and triethylamine (15.0 g, 150 mmol) were combined in a round-bottom flask and dissolved in methylene chloride (50 mL). After cooling in an ice bath, methacryloyl chloride (5.2 g, 50.0 mmol) was slowly added to the solution by syringe. The solution was warmed to room temperature and allowed to stir overnight. Water was added, and the organic phase was washed with sodium bicarbonate solution followed by brine solution. The organic layer was dried over magnesium sulfate and filtered to give a clear solution. After solvent removal, the crude product was purified by passing it through a silica column (1:40 ethyl acetate:hexanes). The product was obtained as a clear liquid, which was stored at 0° C.

Workup

  1. temperatureAfter cooling in an ice bath
  2. washthe organic phase was washed with sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customto give a clear solution
  6. customAfter solvent removal
  7. customthe crude product was purified
  8. customThe product was obtained as a clear liquid, which
  9. customwas stored at 0° C.

Sources & evidence

ORD record
ord-05973da34e664863ab72812c440dc0e5
Source dataset
uspto-grants-2012_08
Patent number
US08241575B2

Reaction notes

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