Oxalic Acid → p-METHOXYCINNAMALDEHYDE

HRID 1110552Notes

Reaction equation

HRID 1110552 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C(NC(C)C)(C)C.C([Li])CCC.[C:23](O)(=O)[C:24](O)=[O:25]>CCCCCC.C(N=CC)(C)(C)C.ClP(=O)(OCC)OCC.O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:23]/[CH:24]=[O:25])=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 312444-MethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 641294p-METHOXYCINNAMALDEHYDE

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 3 days. The following reagents were used: 4-methoxybenzaldehyde (13.5 g). diisopropylamine (32.2 mL), 1.6M n-butyl lithium in hexane (143 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofuran (200 mL). The work up, varied only in that the oxalic acid catalyzed hydrolysis was done overnight at room temperature and then at 85° C. for 2 hours, furnished 12.5 g of crude product which was crystallized from ether-hexane to yield 10 g of (E)-3-(4-methoxyphenyl)-2-propenal, mp 58.5°-60° C.

Workup

  1. customThe compound was prepared
  2. customhydrolysis
  3. waitwas done overnight at room temperature
  4. waitat 85° C. for 2 hours
  5. customfurnished 12.5 g of crude product which
  6. customwas crystallized from ether-hexane

Sources & evidence

ORD record
ord-ad67a1b7714a43ff8773c87c40f1f0ea
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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