Hydrochloric Acid → HCID 21568780, compound

HRID 1579550Notes

Reaction equation

HRID 1579550 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH3:10])[CH2:6][C:5]1=O)(=O)[CH3:2].[CH3:12][CH:13]([C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[C:25]([CH:27]=1)[OH:26])[CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl>C(O)(=O)C>[CH3:12][CH:13]([C:21]1[CH:27]=[C:25]([OH:26])[C:24]2[CH:1]([CH3:2])[C:4]3[CH2:9][CH2:8][CH:7]([CH3:10])[CH2:6][C:5]=3[O:28][C:23]=2[CH:22]=1)[CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 21568772HCID 21568772, compound

Product 1

HCID 21568780HCID 21568780, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.6 g. of 2-acetyl-5 -methylcyclohexanone and 5.6 g. of 5-(1,2-dimethylheptyl)resorcinol in 150 ml. of acetic acid is cooled to 15° and saturated with hydrogen chloride gas. The solution is allowed to warm to 25°, stirred for 20 hours and then heated for one hour on a steam bath. The reaction mixture is concentrated in vacuo, water is added and the residue is dissolved in ethyl acetate. The ethyl acetate solution is washed with water, dried (MgSO4) and concentrated to give a residue which is distilled five times, b.p. 195°-200° (0.025 mm.). The distillate is chromatographed on silica gel with benzene as eluant. The second fraction is collected and distilled to give the title compound, b.p. 190°-195° (0.05 mm.).

Workup

  1. temperatureto warm to 25°
  2. temperatureheated for one hour on a steam bath
  3. concentrationThe reaction mixture is concentrated in vacuo, water
  4. additionis added
  5. dissolutionthe residue is dissolved in ethyl acetate
  6. washThe ethyl acetate solution is washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give a residue which
  10. distillationis distilled five times, b.p. 195°-200° (0.025 mm.)
  11. distillationThe distillate is chromatographed on silica gel with benzene as eluant
  12. customThe second fraction is collected
  13. distillationdistilled

Sources & evidence

ORD record
ord-3f065b8bdf1b4489ac934e850355599c
Source dataset
uspto-grants-1976_01
Patent number
US03931232

Reaction notes

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