Oxalic Acid → 3,3-Bis(4-methylphenyl)-2-propenal

HRID 1110550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110550
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.C(NC(C)C)(C)C.C([Li])CCC.[C:29](O)(=O)[C:30](O)=[O:31]>CCCCCC.C(N=CC)(C)(C)C.ClP(=O)(OCC)OCC.O1CCCC1>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:29][CH:30]=[O:31])=[CH:4][CH:3]=1

Komponenten

9

Edukt 4

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 691484,4'-DimethylbenzophenoneHCID 178418339Butyllithium

Produkt 1

HCID 127223653,3-Bis(4-methylphenyl)-2-propenal

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 13139Diethyl chlorophosphateLösungsmittelHCID 138901N-Ethylidene-2-methylpropan-2-amineLösungsmittel

Versuchsvorschrift

The compound was prepared according to the procedure described in Example 84 except that the reaction was worked up after 30 hours. The following reagents were used: 4,4'-dimethylbenzophenone (21 g), diisopropylamine (32.2 mL), 1.55M n-butyl lithium in hexane (143 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (17.6 mL) and tetrahydrofuran (200 ml). The work up, varied only in that the oxalic acid catalyzed hydrolysis was done overnight at room temperature, furnished 23 g of crude product which was crystallized from hexane to give 18.1 g of 3,3-bis(4-methylphenyl)-2-propenal, mp 92°-93.5° C. Anal Calcd for C17H16O: C, 86.40; H, 6.82 Found: C, 86.48; H, 6.75.

Aufarbeitung

  1. customThe compound was prepared
  2. customhydrolysis
  3. waitwas done overnight at room temperature
  4. customfurnished 23 g of crude product which
  5. customwas crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-3eb9491807aa442d9e330733809847bd
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04975438

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