Hydrochloric Acid → HCID 53979821, compound

HRID 247889Notes

Reaction equation

HRID 247889 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])[CH:7]=[CH:8][C:9]=1[OH:10].[O-]CC.[Na+].[C:20](OCC)(=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13](=[O:15])[CH2:14][C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 141214-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 53979821HCID 53979821, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (1.8 g, 0.078 mole) is dissolved in absolute ethanol (50 ml) under an inert atmosphere. An ethanolic solution of 1-(3'-methoxy-4'-hydroxyphenyl)-1-butene-3-one (5.00 g, 0.026 mole) is then added slowly to the sodium ethoxide solution. The mixture is stirred for 10 minutes, after which diethyl oxalate (3.80 g, 0.026 mole) is added. The reaction is stirred at room temperature for 5 hours and then acidified with concentrated HCl. The mixture is then stirred at 0° C. for 1 hour. The precipitate is collected and dried to afford 4.8 g of ethyl 6-(3'-methoxy-4'-hydroxyphenyl)-2,4-dioxo-5-hexenoate; 63% yield; mp=97°-98° C.

Workup

  1. stirringThe reaction is stirred at room temperature for 5 hours
  2. stirringThe mixture is then stirred at 0° C. for 1 hour
  3. customThe precipitate is collected
  4. customdried

Sources & evidence

ORD record
ord-d7cb4f47877b40f5ba2706d32016cab8
Source dataset
uspto-grants-1993_05
Patent number
US05208251

Reaction notes

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