Triethylamine → 2-Nitrobenzyl acrylate

HRID 1586877Notes

Reaction equation

HRID 1586877 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>CN(C)C1C=CN=CC=1.CC(C)=O>[C:19]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:22])[CH:20]=[CH2:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 119232-Nitrobenzyl alcoholHCID 13140Acryloyl chloride

Product 1

HCID 30164802-Nitrobenzyl acrylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent2×

Procedure

153.2 g (1.0 mole) of 2-nitrobenzyl alcohol, 95.7 g (0.94 mole) of triethylamine and 12.9 g (0.11 mole) of 4-(dimethylamino)pyridine were dissolved in 600 ml of acetone and to the resulting solution, there was dropwise added a solution of 95.0 g (1.05 mole) of acryloyl chloride in 150 ml of acetone at 0° C. over one hour with stirring. Then the stirring was continued for additional one hour. After filtering off the resulting salt, the filtrate was concentrated and purified by column chromatography (packed material: silica gel; eluent: hexane/ethyl acetate=10/1). Thus, 141 g of an oily liquid was recovered.

Workup

  1. filtrationAfter filtering off the resulting salt
  2. concentrationthe filtrate was concentrated
  3. custompurified by column chromatography (packed material: silica gel; eluent: hexane/ethyl acetate=10/1)
  4. customThus, 141 g of an oily liquid was recovered

Sources & evidence

ORD record
ord-8f5538cfec5441eb9698db05736fe40e
Source dataset
uspto-grants-1993_06
Patent number
US05216105

Reaction notes

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