Acetic Acid → HCID 19606408, compound

HRID 1603943Notes

Reaction equation

HRID 1603943 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20]([O:27][CH3:28])(=[O:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23].N1CCNCC1.C(O)(=O)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:21]([C:20]([O:27][CH3:28])=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4837PiperazineHCID 7943Dimethyl malonateHCID 217163814-Methoxy-3-(2-phenylethoxy)benzaldehyde

Product 1

HCID 19606408HCID 19606408, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Methoxy-3-(2-phenylethoxy)benzaldehyde (51.26 g), dimethyl malonate (26.43 g), piperazine (1.70 g) and acetic acid (1.20 g) were refluxed by heating in 300 ml of benzene under azeotropic dehydration conditions for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water, 1 N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was recrystallized from isopropyl ether-dichloromethane to obtain 67.15 g of methyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-methoxycarbonylacrylate.

Workup

  1. washit was washed with water, 1 N hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate
  3. customThe drying agent was separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was recrystallized from isopropyl ether-dichloromethane

Sources & evidence

ORD record
ord-ba927830fa94426cb3bac56c5922598f
Source dataset
uspto-grants-1999_11
Patent number
US05990151

Reaction notes

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