Methane → Methyl 3-(4-formylphenyl)propanoate ethylenedioxy acetal

HRID 986550Notes

Reaction equation

HRID 986550 reaction equation
[CH2:1]1[CH2:19][O:18][O:17][C:4]([O:15][CH3:16])([CH:5]=[CH:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][CH:8]=2)[O:3][O:2]1.C.[H][H]>CO>[CH2:19]1[CH2:1][O:2][O:3][C:4]([O:15][CH3:16])([CH2:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13]=[O:14])=[CH:11][CH:12]=2)[O:17][O:18]1

Participants

5

Reactant 3

HCID 297MethaneHCID 86741941Methyl 4-formylcinnamate ethylenedioxy acetalHCID 178418361HCID 178418361, compound

Product 1

HCID 86741942Methyl 3-(4-formylphenyl)propanoate ethylenedioxy acetalYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-formylcinnamate ethylenedioxy acetal (15.24 g, 0.065 mole, from example 32) in methanol (200 ml) was hydrogenated over 10% palladinised charcoal (0.5 g) until 1 equivalent of hydrogen was absorbed. The filtered solution was then evaporated to give 15.36 g (100%) of an oil, νmax (film), 1730, 1610 cm-1, δ(CDCl3) 2.54 (2H, m, ArCH2), 2.91 (2H, m, CH2CO2), 3.63 (3H, s, ester CH3), 4.00 (4H, m, OCH2CH2O), 5.72 (1H, s, OCHO), 7.25 (4H, ABq, J 10 Hz, Δν19.5 Hz).

Workup

  1. customwas absorbed
  2. customThe filtered solution was then evaporated

Sources & evidence

ORD record
ord-04da27b6ab8c44528c085aa9c625fd72
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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