Hydrochloric Acid → HCID 54360151, compound

HRID 2260751Notes

Reaction equation

HRID 2260751 reaction equation
[CH:1](=O)[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:14]([O:23]CC)(=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CC(C)([O-])C.[K+].Cl>O1CCCC1>[C:14]([CH2:15][C:16](=[CH:1][C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8655SyringaldehydeHCID 31249Diethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 54360151HCID 54360151, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3.6 g of syringaldehyde and 5 ml of diethyl succinate were dissolved in 60 ml of tetrahydrofuran. To the solution was added 4.9 g of potassium t-butoxide, and the mixture was heated under reflux for 24 hours. The mixture was poured into ice water. The aqueous solution was acidified with 6N hydrochloric acid and extracted with 100 ml of ethyl acetate. An organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give 3 g (yield 48%) of ethyl α-carboxymethyl-3,5-dimethoxy-4-hydroxycinnamate. The product was dissolved in 20 ml of N,N-dimethylformamide. To the solution was added 2.1 g of N,N'-dicyclohexylcarbodiimide, and the mixture was stirred at room temperature for 30 minutes. To the mixture was added methanol to filter off an insoluble material, which was washed with methanol and dried to give 2 g (yield 80%) of the corresponding acid anhydride compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with 100 ml of ethyl acetate
  4. washAn organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-c7916c62b8544b509c1673989998abb0
Source dataset
uspto-grants-1995_12
Patent number
US05478856

Reaction notes

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