p-Toluenesulfonic acid → 2-Tetrahydropyranyl 4-(8-cyclohexyloctylamino)benzoate

HRID 903413Notes

Reaction equation

HRID 903413 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][O:25]3)=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 204757724-(8-Cyclohexyloctylamino)benzoic acid

Product 1

HCID 204758342-Tetrahydropyranyl 4-(8-cyclohexyloctylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7 g. of 4-(8-cyclohexyloctylamino)benzoic acid, 2 g. 2,3-dihydropyran and 100 mg. anhydrous p-toluenesulfonic acid in 50 ml. toluene is stirred at room temperature for 20 hours. The solution is washed with saturated sodium bicarbonate, dried, and condensed. The residue is crystallized from methylcyclohexane to white crystals.

Workup

  1. additionA mixture of 7 g
  2. washThe solution is washed with saturated sodium bicarbonate
  3. customdried
  4. customcondensed
  5. customThe residue is crystallized from methylcyclohexane to white crystals

Sources & evidence

ORD record
ord-a57c2055ecb24db0ba45ab2e4e5bf2ae
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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