p-Toluenesulfonic acid → HCID 66604369, compound

HRID 2420173Notes

Reaction equation

HRID 2420173 reaction equation
O[C:2]([O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH2:23][CH:22]2C)([CH:9]1[O:14][CH2:13][CH2:12][N:11]([CH:15]([CH3:17])[CH3:16])[CH2:10]1)C1C=CC=CC=1.[C:29]1(C)[CH:34]=[CH:33][C:32](S(O)(=O)=O)=[CH:31][CH:30]=1.[C:40]1(C)C(C)=CC=CC=1>>[CH:15]([N:11]1[CH2:12][CH2:13][O:14][CH:9]([CH:2]([O:18][C:19]2[CH:20]=[C:21]3[C:25]([C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:23][CH2:22]3)=[CH:26][CH:27]=2)[CH3:40])[CH2:10]1)([CH3:16])[CH3:17]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 20313234HCID 20313234, compound

Product 1

HCID 66604369HCID 66604369, compoundYield 62.7%

Procedure

In 50 ml. of xylene was dissolved 1.5 g. of 2-(1-hydroxy-3-methyl-1-phenyl-5-indanyloxymethyl)-4-isopropylmorpholine and after adding to the solution 5 mg. of p-toluenesulfonic acid, the mixture was refluxed for 3 hours. Then, xylene was distilled off and the residue formed was adsorbed on a silica gel column prepared from 100 ml. of silica gel in chloroform and eluted with ethyl acetate. After removing the first 10 ml. of the ethyl acetate eluate emerging from the column, 200 ml. of the subsequent ethyl acetate eluate was collected and dried to provide 0.9 g. (yield 62.7%) of 4-isopropyl-2-(1-methyl-3-phenyl-6-indenyloxymethyl)morpholine. The citrate of the product had a melting point of 111°-112.5° C.

Workup

  1. distillationThen, xylene was distilled off
  2. customthe residue formed
  3. customprepared from 100 ml
  4. washof silica gel in chloroform and eluted with ethyl acetate
  5. customAfter removing the first 10 ml
  6. customof the subsequent ethyl acetate eluate was collected
  7. customdried
  8. customto provide 0.9 g

Sources & evidence

ORD record
ord-c0fb05b57b1640378ef9e7f30c0a223a
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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