Acetic Acid → HCID 21548776, compound

HRID 1605084Notes

Reaction equation

HRID 1605084 reaction equation
Cl.[C:2]1([CH3:18])[CH:7]=[CH:6][C:5]([C:8]([N:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)N)=[O:9])=[CH:4][CH:3]=1.[CH3:19][CH2:20][O:21][C:22]([CH:24]1[CH2:30][CH2:29][C:27](=O)[CH2:26][CH2:25]1)=[O:23].C(O)(=O)C.Cl>O>[C:2]1([CH3:18])[CH:7]=[CH:6][C:5]([C:8]([N:10]2[C:27]3[CH2:29][CH2:30][CH:24]([C:22]([O:21][CH2:20][CH3:19])=[O:23])[CH2:25][C:26]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 313Hydrochloric AcidHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 21548449HCID 21548449, compound

Product 1

HCID 21548776HCID 21548776, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(4-Toluoyl)-1-phenylhydrazine hydrochloride (13 g.) and 8.7 g. of ethyl cyclohexanone-4-carboxylate (prepared in situ from the corresponding ethylene ketal) in 40 ml. glacial acetic acid, and 5 ml. glacial acetic acid saturated with hydrogen chloride was warmed on a steam bath for thirty minutes, diluted with water and extracted with ether. The ether extracts were washed with potassium bicarbonate solution and water, dried, and evaporated to dryness. The residue was chromatographed on silica gel using 10% ether-pentane as eluant to give 12.7 g. of the title compound; m.p. 70°-72°C. (hexane-ether).

Workup

  1. extractionextracted with ether
  2. washThe ether extracts were washed with potassium bicarbonate solution and water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel using 10% ether-pentane as eluant
  6. customto give 12.7 g

Sources & evidence

ORD record
ord-2b84e4b61f894384b2864f61c0b1ff66
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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