p-Toluenesulfonic acid monohydrate → HCID 14995075, compound

HRID 1460894Notes

Reaction equation

HRID 1460894 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-2231098475b746c7ae5e30f35155a25a
Source dataset
uspto-grants-1991_12
Patent number
US05071988

Reaction notes

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