Hydrochloric Acid → HCID 12257827, compound

HRID 1579552Notes

Reaction equation

HRID 1579552 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])(=O)[CH3:2].C[CH:12]([C:20]1C=C(O)C=C([CH:26]=1)O)[CH:13](C)[CH2:14]CCCC.Cl>C(O)(=O)C>[CH2:9]1[C:4]2[CH2:1][C:2]3[C:14](=[CH:13][CH:12]=[CH:20][CH:26]=3)[O:10][C:5]=2[CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 134002-AcetylcyclohexanoneHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diol

Product 1

HCID 12257827HCID 12257827, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.48 g. of 2-acetylcyclohexanone and 4.17 g. of 5-(1,2-dimethylheptyl)resorcinol in 100 ml. of acetic acid is cooled to 15° and saturated with hydrogen chloride gas. The reaction mixture is allowed to warm to 25° and stirred for 23 hours. The solvent is removed in vacuo, the residue is distilled twice and the fraction boiling at 170°-190° (0.02 mm.) is collected and chromatographed on silica gel with benzene as eluant. The nonpolar fractions are rechromatographed on a silver nitrate impregnated silica gel "dry-column" with 18:1:1 cyclohexaneacetic acid-ether to give a mixture which is separated by distillation to give the title compounds, b.p. 180° (0.005 mm.), tetrahydro xanthene; b.p. 190° (0.003 mm.), aromatic xanthene.

Workup

  1. temperatureto warm to 25°
  2. customThe solvent is removed in vacuo
  3. distillationthe residue is distilled twice
  4. customthe fraction boiling at 170°-190° (0.02 mm.) is collected
  5. customchromatographed on silica gel with benzene as eluant
  6. customThe nonpolar fractions are rechromatographed on a silver nitrate
  7. customto give a mixture which
  8. customis separated by distillation

Sources & evidence

ORD record
ord-2cbeb2e63e5f48e0bb7a33f76e718fa6
Source dataset
uspto-grants-1976_01
Patent number
US03931232

Reaction notes

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