Trimethylamine → HCID 14228144, compound

HRID 2287934Notes

Reaction equation

HRID 2287934 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].CN(C)C.[C:14](Cl)(=[O:17])[CH:15]=[CH2:16]>C(Cl)(Cl)Cl>[C:14]([O:1][CH2:2][C:3]([CH2:8][O:9][C:2](=[O:1])[CH:3]=[CH2:4])([CH3:7])[C:4]([OH:6])=[O:5])(=[O:17])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 13140Acryloyl chlorideHCID 78501Dimethylolpropionic acid

Product 1

HCID 14228144HCID 14228144, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Into a reactor equipped with a stirrer, a thermometer a gas introducing tube and a dropping funnel, 201 g (1.5 mol) of 2,2-bis(hydroxymethyl)propionic acid, 304 g (3.0 mol) of trimethylamine and 600 ml of chloroform were charged. Under ice cooling, 406 g (4.5 mol) of acryloylchloride were dissolved in 400 ml of chloroform, and the resulting solution was added dropwise to the reaction liquid from the dropping funnel while the temperature of the reaction liquid was kept below 5° C. After the completion of dropping, the reaction liquid was kept under ice cooling and stirred for two hours. Chloroform was then removed from the reaction liquid under reduced pressure. Resulting yellow crystals were purified by column chromatography using as a developing solvent ethyl acetate/n-hexane mixed solvent (1:4 by volume). The solvent was then removed under reduced pressure to obtain 2,2-bis(acryloyloxymethyl)propionic acid as white crystals. ##STR17##

Workup

  1. customInto a reactor equipped with a stirrer
  2. additiona thermometer a gas introducing tube and a dropping funnel
  3. additionthe resulting solution was added dropwise to the reaction liquid from the dropping funnel while the temperature of the reaction liquid
  4. customwas kept below 5° C
  5. customthe reaction liquid
  6. customChloroform was then removed from the reaction liquid under reduced pressure
  7. customResulting yellow crystals
  8. customwere purified by column chromatography
  9. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-15711e65a4f3403084b47104231900c7
Source dataset
uspto-grants-2000_07
Patent number
US06087010

Reaction notes

Loading…