Benzyl Alcohol → HCID 178427655, compound

HRID 1974613Notes

Reaction equation

HRID 1974613 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[CH2:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC=CC=1>>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[CH2:23]([O:10][C:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([CH2:2][NH2:1])[CH2:8][CH2:7]1)=[O:11])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 178511262HCID 178511262, compound

Product 1

HCID 178427655HCID 178427655, compoundYield 96%

Procedure

Trans-4-(aminomethyl)-cyclohexane carboxylic acid (50 g (0.318Moles)), p-toluenesulfonic acid (61.7 g (0.324Moles)), benzyl alcohol (250 ML (2.4 Moles)) and toluene (250 ML) were combined and stirred. The resulting mixture was refluxed for 24 hours and the liberated water was removed azeotropically using a Dean-Stark apparatus. A clear solution was obtained after 5 hours of refluxing. The solution was allowed to cool to room temperature and the product crystallized. The mixture was vacuum filtered, washed with ether and dried in a vacuum oven to give 128.12 g (96% yield) of the above-identified product. 1H NMR (CD3OD) d 1.05 (m, 2H), 1.43 (m, 2H), 1.59 (m, 1H), 1.85 (m, 2H), 2.03 (m, 2H), 2.33 (m, 1H), 2.35 (s, 3H), 2.75 (d, 2H), 5.09 (s, 2H), 7.23 (d, 2H), 7.32 (m, 5 H), 7.69 (d, 2H). M.P. 154°-156° C.

Workup

  1. temperatureThe resulting mixture was refluxed for 24 hours
  2. customthe liberated water was removed azeotropically
  3. customA clear solution was obtained after 5 hours
  4. temperatureof refluxing
  5. customthe product crystallized
  6. filtrationfiltered
  7. washwashed with ether
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-18fe8d211e8c42ed9f237db315ced080
Source dataset
uspto-grants-1994_02
Patent number
US05283293

Reaction notes

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