Hydrochloric Acid → HCID 13036788, compound

HRID 223785Notes

Reaction equation

HRID 223785 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])O)=[CH:4][CH:3]=1.[OH-:13].[Na+].Cl.[Cl-].[Na+]>C(OCC)(=O)C.CCCCCC.O>[CH2:9]([CH:7]1[C:2]([OH:6])([CH3:1])[CH:3]=[CH:4][C:5]1=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide3×HCID 10975884HCID 10975884, compound

Product 1

HCID 13036788HCID 13036788, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
40 °C

Procedure

In a reaction vessel, water (40 ml) and 5-methyl-2-furyl-n-butylcarbinol (0.5 g) were charged, and the pH value was regulated to 5 with an aqueous 1 N NaOH solution and an aqueous 1 N HCl solution. The temperature was elevated up to 100° C. to reflux, and the mixture was stirred under reflux for 30 hours while maintaining a pH value of 5 to 5.5 by the addition of an aqueous 1 N NaOH solution and an aqueous 1 N HCl solution. After cooling to 40° C., the reaction mixture was neutralized with an aqueous 1 N NaOH solution, and sodium chloride (12 g) was added thereto. The mixture was extracted with toluene (40 ml) five times. From the extract, toluene was removed by distillation at 60° C. under reduced pressure to give an oily substance (0.48 g), which was subjected to a thin layer chromatography on silica gel with a mixture of ethyl acetate-n-hexane (1:2 by volume) as the developing solvent. The objective part of the silica gel layer was collected by scraping and eluted with ethyl acetate. The silica gel was eliminated by filtration, and the filtrate was concentrated to obtain 2-n-butyl-3-hydroxy-3-methyl-4-cyclopentenone (3.5 g). Yield, 70%. NMR spectrum (CCl4, internal standard TMS, δ ppm, 60 MHz): 7.25 (d, 1H, 4-H); 5.85 (d, 1H, 5-H); 3.63 (broad s, 1H, 3--OH); 2.20 (m, 1H, 2-H); 1.25 (s, 3H, 3-CH3).

Workup

  1. customwas elevated up to 100° C.
  2. temperatureto reflux
  3. temperatureunder reflux for 30 hours
  4. temperaturewhile maintaining a pH value of 5 to 5.5
  5. additionwas added
  6. extractionThe mixture was extracted with toluene (40 ml) five times
  7. customFrom the extract, toluene was removed by distillation at 60° C. under reduced pressure
  8. customto give an oily substance (0.48 g), which
  9. customThe objective part of the silica gel layer was collected
  10. washeluted with ethyl acetate
  11. filtrationThe silica gel was eliminated by filtration
  12. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-03fc0fc2c80c455db88bc318b140cb19
Source dataset
uspto-grants-1982_10
Patent number
US04356326

Reaction notes

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