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

HRID 2232795Notes

Reaction equation

HRID 2232795 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 13139Diethyl chlorophosphateSolventHCID 138901N-Ethylidene-2-methylpropan-2-amineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-be12909759ac48e9b5d51d35cd5dbcec
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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