Benzyl Alcohol → HCID 21515609, compound

HRID 1284059Notes

Reaction equation

HRID 1284059 reaction equation
[CH3:1][C:2]1[N:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]([CH3:19])=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(O)[C:27]1[CH:32]=[CH:31]C=[CH:29][CH:28]=1>OS(O)(=O)=O>[CH3:1][C:2]1[N:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]([CH3:19])=[C:5]([C:14]([O:16][CH2:17][C:18]2[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=2)=[O:15])[C:6](=[O:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 21515601HCID 21515601, compound

Product 1

HCID 21515609HCID 21515609, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

4 g. of 2,6-dimethyl-3,5-dicarboethoxy-N-phenyl-4-pyridone (prepared as described in Example 1) were dissolved in 20 ml. of benzyl alcohol, 4 drops of concentrated H2SO4 were added and the mixture was stirred and heated for 7 hours at 130°, at the same time distilling off the produce ethanol. The benzyl alcohol solution was washed with a saturated solution of sodium bicarbonate and the slurry was extracted several times with chloroform. The extracts were combined and dried over magnesium sulphate, and the chloroform was distilled off in vacuo. The oily residue was dissolved in 50 ml. of ether and 50 ml. of petrolether 40'-60° were added. After cooling in a dry ice-acetone bath and scratching, 2,5g. of 2,6-dimethyl-3-carboethoxy-5-carbobenzyloxy-N-phenyl-4-pyridone, m.p. 142° were obtained.

Workup

  1. temperatureheated for 7 hours at 130°, at the same time
  2. distillationdistilling off the produce ethanol
  3. washThe benzyl alcohol solution was washed with a saturated solution of sodium bicarbonate
  4. extractionthe slurry was extracted several times with chloroform
  5. dry with materialdried over magnesium sulphate
  6. distillationthe chloroform was distilled off in vacuo
  7. dissolutionThe oily residue was dissolved in 50 ml
  8. additionof petrolether 40'-60° were added
  9. temperatureAfter cooling in a dry ice-acetone bath

Sources & evidence

ORD record
ord-3bfbf5e297a449428184f4f3b52f5f20
Source dataset
uspto-grants-1976_08
Patent number
US03978072

Reaction notes

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