p-Toluenesulfonic acid → HCID 27234258, compound

HRID 1077150

Reaction equation

HRID 1077150 reaction equation
C(OC1C=C(CCCC(=O)[CH2:15][CH2:16][C:17]2([CH3:24])[C:21](=O)[CH2:20][CH2:19][C:18]2=[O:23])C=CC=1)(=O)C.C([O:29][C:30]1[CH:31]=[C:32]([CH2:36][CH2:37][CH2:38][C:39](=O)CCN(CC)CC)[CH:33]=[CH:34][CH:35]=1)(=O)C.C(OC1C=C(CCCC(=O)C=C)C=CC=1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOCC>[CH3:24][C@:17]12[CH2:16][CH2:15][C:39]3[C:33]4[CH:34]=[CH:35][C:30]([OH:29])=[CH:31][C:32]=4[CH2:36][CH2:37][C:38]=3[C:21]1=[CH:20][CH2:19][C:18]2=[O:23]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 214854206-m-Acetoxyphenyl-1-diethylaminohexan-3-oneHCID 214855806-m-Acetoxyphenylhex-1-en-3-oneHCID 21485772HCID 21485772, compound

Product 1

HCID 27234258HCID 27234258, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

Reflux 2-(6-m-acetoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione (0.8 g, the product of Michael condensation of 2-methylcyclopentanedione and a mixture of 6-m-acetoxyphenyl-1-diethylaminohexan-3-one and 6-m-acetoxyphenylhex-1-en-3-one, and containing some of the corresponding free phenolic compound) in benzene (25 cc) with toluene-p-sulfonic acid (0.3 g) for 50 minutes. On cooling add ether (50 cc) and wash the mixture in turn with water, saturated aqueous potassium bicarbonate, and brine; dry over anhydrous magnesium sulfate. The residue after removal of solvent is a purple gum (0.6 g), part of which can be induced to crystallize. Dissolve a portion (0.45 g) of this gum in benzene and adsorb on an activated Fuller's earth (40 g); elute with benzene to obtain 13β-methyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17-one, which one recrystallizes from diisopropyl ether, m.p. 225°-226°; ultraviolet absorption peak at 312.5 mμ (ε23,000); infrared absorption peaks at 2.99 μ, 5.81 μ, and 8.00μ.

Workup

  1. temperatureOn cooling
  2. washwash the mixture in turn with water, saturated aqueous potassium bicarbonate, and brine
  3. dry with materialdry over anhydrous magnesium sulfate
  4. customThe residue after removal of solvent
  5. customto crystallize
  6. dissolutionDissolve a portion (0.45 g) of this gum in benzene
  7. washelute with benzene

Sources & evidence

ORD record
ord-ff41c2cd4a0240ac8b97c3e893e2ffde
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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