Benzyl Alcohol → HCID 178427655, compound

HRID 264004Notes

Reaction equation

HRID 264004 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) of 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. The mixture was refluxed for 24 hours and the liberated water was removed azeotropically by means of 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.). Reference: Greenstein, Jesse P.; Winitz, Milton. Chemistry of the Amino Acids. vol. 2, (1986), 942. 1H NMR (CD3OD) δ1.05 (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.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customthe liberated water was removed azeotropically by means of a Dean-Stark apparatus
  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
  9. customto give 128.12 g (96% yield.)

Sources & evidence

ORD record
ord-0167ebf47c9d454daea3a3b32f007d46
Source dataset
uspto-grants-1997_07
Patent number
US05646165

Reaction notes

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