2,4-Dimethoxybenzaldehyde → HCID 13051245, compound

HRID 980842Notes

Reaction equation

HRID 980842 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13](O)(=[S:17])[CH:14](C)O.[CH:19]([O-:21])=O.[NH4+:22]>O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]1[NH:22][C:19](=[O:21])[CH:13]([CH3:14])[S:17]1

Participants

6

Reactant 3

HCID 691752,4-DimethoxybenzaldehydeHCID 2723923Ammonium formateHCID 178473673HCID 178473673, compound

Product 1

HCID 13051245HCID 13051245, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1140TolueneSolvent

Procedure

In a flask equipped with a trap for the continuous collection and removal of water and condenser, 40 g (0.24 mole) 2,4-dimethoxybenzaldehyde, 26.8 g (0.24 mole) 95% thiolactic acid, 15.2 g (0.24 mole) ammonium formate and 200 ml toluene were placed. The resulting mixture was heated to reflux and refluxed for 4 hours, during which about 10 ml water were collected. The reaction mixture was then allowed to stir overnight without heat at ambient temperature. An orange precipitate formed overnight. The reaction mixture was poured into water and then extracted three times with ethyl acetate. The combined organic fractions were washed twice with an aqueous potassium carbonate solution, once with water, dried, and filtered. Stripping gave a yellow semi-solid which washed with ether to give 20 g of the above-identified product as a fluffy yellow solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. customwere collected
  4. customAn orange precipitate formed overnight
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic fractions were washed twice with an aqueous potassium carbonate solution, once with water
  7. customdried
  8. filtrationfiltered
  9. customStripping gave a yellow semi-solid which
  10. washwashed with ether

Sources & evidence

ORD record
ord-1012aed03f284a6189acaa6875c05e46
Source dataset
uspto-grants-1987_01
Patent number
US04639460

Reaction notes

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