Phenol → HCID 12899700, compound

HRID 1680813Notes

Reaction equation

HRID 1680813 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[ClH:12].[C:13]([CH:18]1[C:23](=O)[CH2:22][CH2:21][NH:20][CH2:19]1)(OCC)=[O:14].OS(O)(=O)=O.C1(O)C=CC=CC=1.[NH4+].[OH-]>C(Cl)(Cl)Cl>[ClH:12].[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:23]3[CH2:22][CH2:21][NH:20][CH2:19][C:18]=3[C:13](=[O:14])[O:11][C:5]=2[CH:4]=1

Participants

7

Reactant 5

HCID 996Phenol2×HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 162513,4-DimethoxyphenolHCID 1073153-Piperidinecarboxylic acid, 4-oxo-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 12899700HCID 12899700, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 46.0 g (0.3 m) of 3,4-dimethoxyphenol and 41.7 g (0.2 m) of 3-carbethoxy-4-piperidone HCl was cooled in an ice bath and treated with 100 cc of 73% v/v H2SO4 in 1/2 hr with stirring and protection from moisture. After stirring 4 days at room temperature the reaction was chilled and treated with an additional 24 g (0.156 m) of the phenol. After 5 days a second 24 g portion of the phenol was added. After stirring 6 days the reaction was treated with 150 g of ice and conc. NH4OH to pH 8-9. The resultant gum was stirred with 150 cc CHCl3 for 1/2 hr and was filtered. The filtrate was evaporated and the resultant gum was triturated with pet ether followed by ethyl ether. The resultant solid was crystallized from 150 cc 3 N HCl affording 33.4 g of the pyridin-5 -one as the hydrochloride, mp 254°-6° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringAfter stirring 4 days at room temperature the reaction
  3. temperaturewas chilled
  4. stirringAfter stirring 6 days the reaction
  5. filtrationwas filtered
  6. customThe filtrate was evaporated
  7. customthe resultant gum was triturated with pet ether
  8. customThe resultant solid was crystallized from 150 cc 3 N HCl affording 33.4 g of the pyridin-5 -one as the hydrochloride, mp 254°-6° C.

Sources & evidence

ORD record
ord-e2fa9d9eb1d84dc4a84110856883dd92
Source dataset
uspto-grants-1981_06
Patent number
US04276296

Reaction notes

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