p-Toluenesulfonic acid → HCID 86733808, compound

HRID 1283132Notes

Reaction equation

HRID 1283132 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH:4]([C:6]1([OH:18])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:5].[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([OH:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1>CC(C)=O.CCOCC>[CH3:19][N:2]([CH3:1])[CH2:3][CH:4]([C:6]1([OH:18])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:5].[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([OH:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21519258HCID 21519258, compound

Product 1

HCID 86733808HCID 86733808, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.6 g 1-(2-Dimethylamino-1-methylethyl)-2-phenylcyclohexanol (Example I) in 30 ml acetone is added to a solution of 3.6 g p-toluenesulfonic acid. The solution is seeded and diluted after a few minutes with 75 ml dry ether to give 5 g crude product which is recrystallized from 50 ml acetone to give 4.2 product, m. 140°-2°.

Sources & evidence

ORD record
ord-22d2beb1793340969a6f2d984b8e61d0
Source dataset
uspto-grants-1976_08
Patent number
US03974157

Reaction notes

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