Benzyl Alcohol → HCID 178427655, compound

HRID 2380396Notes

Reaction equation

HRID 2380396 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 3

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

Product 1

HCID 178427655HCID 178427655, compoundYield 94,255%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trans-4-(aminomethyl)-cyclohexane carboxylic acid (50 g (0.318 moles)), p-toluenesulfonic acid (61.7 g (0.324 mmoles)), 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) δ1.05 (, 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, 5H), 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-573d889713bf4fa1882d47fdefd95d77
Source dataset
uspto-grants-1994_11
Patent number
US05367072

Reaction notes

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