Benzyl Alcohol → HCID 178427655, compound

HRID 861569Notes

Reaction equation

HRID 861569 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 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 g (0.318 moles) trans-4-(aminomethyl)-cyclohexane carboxylic acid, 61.7 g (0.324 moles) p-toluenesulfonic acid, 250 mL (2.4 moles) benzyl alcohol, and 250 mL toluene were combined and stirred at room temperature. The mixture was refluxed for 24 hours and the liberated water removed azeotropically by means of a Dean and 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). 1H NMR (CD3OD) δ 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, 5H), 7.69 (d, 2H). M.P. 154°-156° C. See, Greenstein and Winitz, Chemistry of the Amino Acids. 2: 942 (1986).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customthe liberated water removed azeotropically by means of a Dean and Stark apparatus
  3. customA clear solution was obtained after 5 hours
  4. temperatureof refluxing
  5. temperatureto cool to room temperature
  6. customthe product crystallized
  7. filtrationfiltered
  8. washwashed with ether
  9. customdried in a vacuum oven
  10. customto give 128.12 g (96% yield)

Sources & evidence

ORD record
ord-0e48a708b02d4af5bd616d881d522df5
Source dataset
uspto-grants-1998_02
Patent number
US05714580

Reaction notes

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