Water → HCID 14988338, compound

HRID 1087145Notes

Reaction equation

HRID 1087145 reaction equation
[CH2:1](Cl)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][NH:12][CH2:13][CH2:14][OH:15].O>C(O)C>[CH3:11][N:12]([CH2:13][CH2:14][OH:15])[CH2:1]/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 14988338HCID 14988338, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.5 Grams of cinnamyl chloride and 21 g of 2-methylaminoethanol were dissolved in 100 ml of ethanol, and the solution was refluxed for 5 hours. The solvent was removed by evaporation, to the residue thus obtained was added water and washed with n-hexane. To the water layer was added 3N-sodium hydroxide aqueous solution to adjust its pH to 10-11, and extracted with ether. The ether extract was washed with water and dried with anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue was purified by means of a silica gel column chromatography (eluent: chloroform:methanol=25:1) to yield 15 g of 2-[N-methyl-N-(3-phenyl-2(E)-propenyl)amino]ethanol.

Workup

  1. temperaturethe solution was refluxed for 5 hours
  2. customThe solvent was removed by evaporation, to the residue
  3. customthus obtained
  4. washwashed with n-hexane
  5. additionTo the water layer was added 3N-sodium hydroxide aqueous solution
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. washwas washed with water
  9. dry with materialdried with anhydrous sodium sulfate
  10. customthe solvent was removed by evaporation
  11. customThe residue was purified by means of a silica gel column chromatography (eluent: chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-81fc35911cb34749812460100a92e006
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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