Triethylamine → 6-Bromohexyl prop-2-enoate

HRID 263827Notes

Reaction equation

HRID 263827 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18]>C1C=CC=CC=1>[C:16]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])(=[O:19])[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 779706-Bromo-1-hexanol

Product 1

HCID 151538196-Bromohexyl prop-2-enoateYield 65.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Into a reactor, 30 g of 6-bromo-1-hexanol, 18.4 g of triethylamine, and 500 ml of benzene were charged, to which a solution of 16.5 g of acryloyl chloride in 200 ml of benzene was added dropwise, while stirring and cooling with ice, and stirred for 3 hours to give a reaction solution. The reaction solution was washed with a 3N-HCl and then with water, dried over sodium sulfate anhydride, and thereafter the solvent was evaporated and the residue was purified by the silica gel column chromatography (eluent; toluene) to give 25.4 g (Y., 65.1%) of 6-bromohexyl acrylate. GC; 95.9%

Workup

  1. additionwas added dropwise
  2. temperaturecooling with ice
  3. stirringstirred for 3 hours
  4. customto give a reaction solution
  5. washThe reaction solution was washed with a 3N-HCl
  6. dry with materialwith water, dried over sodium sulfate anhydride
  7. customthe solvent was evaporated
  8. customthe residue was purified by the silica gel column chromatography (eluent; toluene)

Sources & evidence

ORD record
ord-673df968ccc84d87a1da24d43e9a0ad1
Source dataset
uspto-grants-1997_07
Patent number
US05645760

Reaction notes

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