Ethyl Acetate → Methyl 4-(3-oxoprop-1-en-1-yl)benzoate

HRID 2198790Notes

Reaction equation

HRID 2198790 reaction equation
[Br-].[CH:2]([C:4]1C=CC=CC=1[P+](C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:3].[C:24]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([O:26][CH3:27])=[O:25].C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:24]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[CH:4][CH:2]=[O:3])=[CH:30][CH:29]=1)([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 15294Methyl 4-FormylbenzoateHCID 86738613HCID 86738613, compound

Product 1

HCID 53758591Methyl 4-(3-oxoprop-1-en-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hours. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm1 (COOCH3), 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, 1), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, 1), and 9.8 (d, --CHO, 1 ). Analysis calculated for C11H10O3 :C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.26%.

Workup

  1. customAfter evaporating toluene under reduced pressure
  2. customthe residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant
  3. customThe second fraction obtained

Sources & evidence

ORD record
ord-b7b99ef037e440a3b50b1cfb8248dec4
Source dataset
uspto-grants-1982_11
Patent number
US04359568

Reaction notes

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