Hydrochloric Acid → Ethyl 6-(3-methoxy-4-hydroxyphenyl)-2,4-dioxo-5-hexenoate

HRID 2352637Notes

Reaction equation

HRID 2352637 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 53979821Ethyl 6-(3-methoxy-4-hydroxyphenyl)-2,4-dioxo-5-hexenoateYield 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-c596711422a943e78fdde31c22c3b482
Source dataset
uspto-grants-1989_10
Patent number
US04877881

Reaction notes

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