p-Toluenesulfonic acid → HCID 18952706, compound

HRID 1741929Notes

Reaction equation

HRID 1741929 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]1([CH:18]2[CH2:23][CH2:22][C:21](=[C:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(Cl)Cl.[CH3:33][OH:34].[C:35]([O-:38])(O)=O.[Na+]>C(Cl)Cl.CO>[CH3:33][O:34][C:27]1([O:38][CH3:35])[CH2:28][CH2:29][C:24](=[C:21]2[CH2:20][CH2:19][CH:18]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:23][CH2:22]2)[CH2:25][CH2:26]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 10752979HCID 10752979, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 18952706HCID 18952706, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A catalytic mount of p-toluenesulfonic acid (26 mg) was added to a solution of 4-(4'-cyclohexylcyclohexylidene)cyclohexane (2", 2"-dimethyltrimethylene)ketal (5.56 g) in 1:1 methylene chloride-methanol (400 ml). TLC after three hours indicated the reaction to be about 50% complete. Additional methanol (200 ml) was added and the reaction checked by TLC after another two hours. About 10% of starting material remained. The reaction was worked up at this time by the addition of more CH2Cl2 followed by saturated aqueous NaHCO3 solution. The mixture was shaken and the layers were separated. The aqueous layer was extracted two more times with CH2Cl2, the pooled CH2Cl2 extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to a solid. This dimethyl ketal was used without further purification.

Workup

  1. customthe reaction
  2. waitthe reaction checked by TLC after another two hours
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted two more times with CH2Cl2
  5. washthe pooled CH2Cl2 extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customThis dimethyl ketal was used without further purification

Sources & evidence

ORD record
ord-78922a7ee91b4eaf881b78dffe6fa62b
Source dataset
uspto-grants-1994_08
Patent number
US05334712

Reaction notes

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