Acetic Acid → HCID 18541324, Verbindung

HRID 411738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411738
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[C:19]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.O>[CH2:24]([O:23][C:21](=[O:22])[C:20](=[CH:10][C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C:3]2[C:2]([Cl:1])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:18])=[CH:7][CH:8]=1)[C:19]([O:27][CH2:28][CH3:29])=[O:26])[CH3:25]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 7354664-[(2,6-dichlorobenzyl)oxy]benzaldehyde

Produkt 1

HCID 18541324HCID 18541324, VerbindungAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-(2,6-dichlorobenzyloxy)benzaldehyde (5.62 g, 20 mmol) and diethyl malonate (3.52 g, 22 mmol) in benzene (75 mL), were added piperidine (90 μL) and glacial acetic acid (0.25 mL). After refluxing for 24 h with azeotropic water removal, the cooled reaction was concentrated in vacuo then partitioned between ether and water. The organic extract was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution, water, brine and dried (MgSO4). Removal of volitiles in vacuo afforded the crude title compound (8.35 g, 97%) which was used in the next step without farther purification.

Aufarbeitung

  1. customthe cooled reaction
  2. concentrationwas concentrated in vacuo
  3. customthen partitioned between ether and water
  4. extractionThe organic extract
  5. washwas washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution, water, brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of volitiles in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-08e06f6473a74a6d97f90567fea30d64
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559179B1

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