p-Toluenesulfonic acid monohydrate → HCID 14995075, compound

HRID 1587574Notes

Reaction equation

HRID 1587574 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.O.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:21][O:16][C:15](=[O:17])[CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:19][CH:18]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18956587HCID 18956587, compound

Product 1

HCID 14995075HCID 14995075, compoundYield 573.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the acid (8.56 g, 33.4 mmole) of Step E and p-toluenesulfonic acid monohydrate (1.05 g, 5.6 mmole) in methanol (70 mL) is refluxed for 2.5 hours (TLC, methanol-toluene 1:9). The methanol is evaporated and the residue is dissolved in ethyl acetate and washed with brine. After drying (MgSO4) the solvent is removed to yield a tan solid (8.68 g, 96.2%, m.p. 111°-113° C.). The crude product is used as such in the next step.

Workup

  1. customThe methanol is evaporated
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialAfter drying (MgSO4) the solvent
  5. customis removed

Sources & evidence

ORD record
ord-0e4071a9b0fe4a99b7ad65f9c12950e4
Source dataset
uspto-grants-1993_06
Patent number
US05218124

Reaction notes

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