Ethyl Acetate → HCID 19757203, compound

HRID 1588132Notes

Reaction equation

HRID 1588132 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15][CH2:16][O:17][CH3:18])[C:4]=1[CH2:19][CH:20]1C(=O)O[C:23](C)([CH3:27])[O:22][C:21]1=[O:29].C(OCC)(=O)C>C(O)C.N1C=CC=CC=1.[Cu]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15][CH2:16][O:17][CH3:18])[C:4]=1[CH2:19][CH2:20][C:21]([O:22][CH2:23][CH3:27])=[O:29]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 197571901-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]-1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)methane

Product 1

HCID 19757203HCID 19757203, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

4.07 Grams of 1-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]-1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)methane was dissolved in 20 ml of ethanol and 40 ml of pyridine, then a catalytic amount of copper powder was added thereto and refluxed for 10 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure, to the residue thus obtained was added 20 ml of ethyl acetate. The organic layer was washed with a diluted hydrochloric acid, water, a saturated sodium chloride aqueous solution in this order, dried over anhydrous sodium sulfate, concentrated under a reduced pressure to yield 3.42 g of ethyl 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propionate as an ethyl ester. Colorless oily substance.

Workup

  1. temperaturerefluxed for 10 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure, to the residue
  4. customthus obtained
  5. washThe organic layer was washed with a diluted hydrochloric acid, water
  6. dry with materiala saturated sodium chloride aqueous solution in this order, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-0a79a26e272341fab642d4cbd9d16798
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

Loading…