Sulfuric Acid → Ethyl 4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamate

HRID 484012Notes

Reaction equation

HRID 484012 reaction equation
O[C:2]1[C:7]([CH2:8][C:9]2[CH:22]=[CH:21][C:12]([CH:13]=[C:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:23][C:24]1[C:30]([CH3:31])=[C:29]([OH:32])[C:28]([CH3:33])=[CH:27][C:25]=1[OH:26].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:33][C:28]1[C:29](=[O:32])[C:30]([CH3:31])=[C:24]([CH3:23])[C:25](=[O:26])[C:27]=1[CH:8]([C:7]1[CH:2]=[N:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[CH:22]=[CH:21][C:12]([CH:13]=[C:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 12785TrimethylhydroquinoneHCID 516892Sodium BicarbonateHCID 178471253HCID 178471253, compound

Product 1

HCID 57139798Ethyl 4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamateYield 83.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1.0 g (3.36 mmol) of ethyl 4-[hydroxy-(3-pyridyl)]methyl-α-methylcinnamate in 10 ml of dichloroethane, 514 mg (3.38 mmol) of 2,3,5-trimethylhydroquinone and 0.28 ml (5.26 mmol) of concentrated sulfuric acid were added and refluxed by heating for 2 hours. The reaction mixture was made weakly alkaline with a saturated solution of sodium hydrogen carbonate, and the organic phase was separated while the aqueous phase was extracted with chloroform and the extract was combined with the organic phase. The organic phase was oxidized with ferric chloride, washed with water, dried, and concentrated. The residue was purified with silica gel column chromatography (isopropyl ether-acetic ester (1:1)), to give 1.2 g (yield 82.7%) of ethyl 4-[3,5,6-trimethyl-1,4-benzoquinon -2-yl(3-pyridyl)methyl]-α-methylcinnamate. The physical data are shown in Table 1.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 2 hours
  3. customthe organic phase was separated while the aqueous phase
  4. extractionwas extracted with chloroform
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography (isopropyl ether-acetic ester (1:1))

Sources & evidence

ORD record
ord-fa359ef243d14161b5ae245b53f0136c
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Reaction notes

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