p-Toluenesulfonic acid → Tetrahydropyranyl 4-(hexadecylamino)benzoate

HRID 126946

Reaction equation

HRID 126946 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)=[O:23])=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 472634-(Hexadecylamino)benzoic acid

Product 1

HCID 23457765Tetrahydropyranyl 4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7 g. (19.4 m moles) 4-(hexadecylamino)-benzoic acid, 2 g. (23.8 m moles) 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-5b97b065307b4273b4b790f7d8eaaaf6
Source dataset
uspto-grants-1981_03
Patent number
US04254138

Linked notes

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