Hydrochloric Acid → HCID 86746629, compound

HRID 1613934Notes

Reaction equation

HRID 1613934 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][CH:8]([C:17]1[C:26]([CH3:27])=[C:25]([O:28]C(=O)C)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CO.Cl>O>[OH:7][CH:8]([C:17]1[CH:26]([CH3:27])[C:25](=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 15007057HCID 15007057, compound

Product 1

HCID 86746629HCID 86746629, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 502 mg (3.63 mmols) of potassium carbonate in 2 ml of water was added to a solution of 1.23 g (3.63 mmols) of 2 (trans-1-hydroxy-2-nonenyl)-3-methyl-4-acetoxyquinoline, 15 ml of water and 80 ml of methanol and stirred at room temperature for 10 minutes. After neutralization by addition of 1N hydrochloric acid, the solvent was distilled off under reduced pressure and 30 ml of chloroform was added to the resultant residue, followed by washing with water and drying with sodium sulfate. The solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=1:2) to obtain 746 mg (yield 69%) of 2-(trans-1-hydroxy-2-nonenyl)-3-methyl-4-quinolone.

Workup

  1. distillationthe solvent was distilled off under reduced pressure and 30 ml of chloroform
  2. additionwas added to the resultant residue
  3. washby washing with water
  4. dry with materialdrying with sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=1:2)

Sources & evidence

ORD record
ord-aca3596c471a4e699b92340d35f72c80
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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