Oxalic Acid → 3,3-Bis(3-methoxyphenyl)-2-propenal

HRID 1110488Notes

Reaction equation

HRID 1110488 reaction equation
CO[C:3]1([O:17][CH3:18])[CH:16]=[CH:15][CH:14]=[C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)[CH2:4]1.C(NC(C)C)(C)C.C([Li])CCC.[C:31]([OH:36])(=O)[C:32](O)=O.ClP(=O)(OCC)[O:39][CH2:40]C>CCCCCC.C(N=CC)(C)(C)C.O1CCCC1>[CH3:40][O:39][C:12]1[CH:13]=[C:8]([C:6]([C:5]2[CH:14]=[CH:15][CH:16]=[C:3]([O:17][CH3:18])[CH:4]=2)=[CH:32][CH:31]=[O:36])[CH:9]=[CH:10][CH:11]=1

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 13139Diethyl chlorophosphateHCID 221554053,3-DimethoxybenzophenoneHCID 178418339Butyllithium

Product 1

HCID 145472293,3-Bis(3-methoxyphenyl)-2-propenal

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 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: 3,3-dimethoxybenzophenone (48.5 g), diisopropylamine (64.4 mL). 1.55M n-butyl lithium in hexane (286 mL), acetaldehyde N-tertbutylimine (29.5 mL), diethyl chlorophosphonate (33.2 mL) and tetrahydrofurane (400 mL). The work up varied only in that the oxalic acid catalyzed hydrolysis was done at 85° C. over two hours, furnished 53 g of essentially pure 3,3-bis(3-methoxyphenyl)-2-propenal as a pale yellow oil.

Workup

  1. customThe compound was prepared
  2. customhydrolysis
  3. waitwas done at 85° C. over two hours

Sources & evidence

ORD record
ord-0329ed7c4c3948ebacf9f1b7e09166d3
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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