p-Toluenesulfonic acid → HCID 19776909, compound

HRID 1612872Notes

Reaction equation

HRID 1612872 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([S:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:17]=2[CH:25]=[O:26])=[C:7]([C:12]=1[O:13][CH3:14])[C:8]([O:10]C)=[O:9])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[K+]>CO>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([S:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:17]=2[CH2:25][OH:26])=[C:7]([C:12]=1[O:13][CH3:14])[C:8]([OH:10])=[O:9])=[O:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14797Potassium HydroxideHCID 19776920HCID 19776920, compound

Product 1

HCID 19776909HCID 19776909, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

302 mg (0.8 mol) of the compound from Example 17 are dissolved in 4.6 ml of methanol and stirred at 25° C. with 36 mg of p-toluenesulphonic acid for 1 h. After addition of 0.45 g of potassium hydroxide, the mixture is heated under reflux overnight. It is concentrated in vacuo, and the residue is adjusted to pH=3 using dilute hydrochloric and washed with ethyl acetate. The organic phase is dried using sodium sulphate and concentrated in vacuo.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. concentrationIt is concentrated in vacuo
  4. additionusing dilute hydrochloric
  5. washwashed with ethyl acetate
  6. customThe organic phase is dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d74ec52587644d9be908a3ff34af22f
Source dataset
uspto-grants-1993_03
Patent number
US05190971

Reaction notes

Loading…