Hydrochloric Acid → 4-(6-Acryloyloxyhexyloxy)cinnamic acid

HRID 1356929Notes

Reaction equation

HRID 1356929 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1.CN(C)C1C=CC=CC=1.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31].Cl>O1CCCC1>[C:29]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:18][CH:19]=1)(=[O:32])[CH:30]=[CH2:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 13140Acryloyl chlorideHCID 673232894-(6-Hydroxyhexyloxy)cinnamic acid

Product 1

HCID 600674344-(6-Acryloyloxyhexyloxy)cinnamic acidYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The resulting 4-(6-hydroxyhexyloxy)cinnamic acid (6 g, 0.023 mole) and N,N-dimethylaniline (6.6 g, 0.054 mole) were dissolved in tetrahydrofuran (50 mL), and to this mixture was further added dropwise a solution prepared by dissolving acryloyl chloride (4.4 g, 0.049 mole) in tetrahydrofuran (20 mL). After this addition, the mixture was stirred for 4 hours. Then, the reaction solution was poured into 10% hydrochloric acid, and deposited crystal was filtrated off. The resulting coarse crystal was dissolved in ethyl acetate (100 mL), and an organic layer was washed with saturated saline solution and dried over magnesium sulfate. The organic solvent was distilled off under reduced pressure, and then the coarse crystal was re-crystallized (n-hexane-ethyl acetate) to obtain 4-(6-acryloyloxyhexyloxy)cinnamic acid (3.9 g, 54%) in the form of a colorless crystalline powder.

Workup

  1. additionto this mixture was further added dropwise a solution
  2. customprepared
  3. additionAfter this addition
  4. filtrationwas filtrated off
  5. dissolutionThe resulting coarse crystal was dissolved in ethyl acetate (100 mL)
  6. washan organic layer was washed with saturated saline solution
  7. dry with materialdried over magnesium sulfate
  8. distillationThe organic solvent was distilled off under reduced pressure
  9. customthe coarse crystal was re-crystallized (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f03a4c449ee84d38a6772b9474118bbc
Source dataset
uspto-grants-2003_07
Patent number
US06589445B2

Reaction notes

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