Methyl p-toluenesulfonate → HCID 22407755, compound

HRID 439689Notes

Reaction equation

HRID 439689 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:8]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:24]1([CH3:35])[CH:29]=[CH:28][C:27]([S:30]([O:33]C)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(#N)C>[S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:35])=[CH:25][CH:26]=1)([O-:33])(=[O:32])=[O:31].[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:8]([O:10][CH2:11][CH2:12][N+:13]([CH3:24])([CH3:15])[CH3:14])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 15277883HCID 15277883, compound

Product 1

HCID 22407755HCID 22407755, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 16.07 g (50 mmol) of 2-dimethylaminoethyl 3,5-di-tert-butyl-4-hydroxybenzoate, prepared as described in Example 1, 9.31 g (50 mmol) of methyl p-toluenesulfonate and 125 ml of acetonitrile was heated at reflux for 1 hr. The mixture was cooled and filtered. The collected solid was recrystallized from 1 liter of acetonitrile to give 17.15 g (67.56% of theory) of product; mp=233.5°-236.5° C.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 1 hr
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. customThe collected solid was recrystallized from 1 liter of acetonitrile
  7. customto give 17.15 g (67.56% of theory) of product

Sources & evidence

ORD record
ord-e93e811faef841cbba2bc195faf113c2
Source dataset
uspto-grants-1996_05
Patent number
US05516616

Reaction notes

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