Benzyl Alcohol → HCID 178511263, compound

HRID 1418290Notes

Reaction equation

HRID 1418290 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(O)(=O)=O)=[CH:14][CH:13]=1.C(O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:22]([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:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

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

Product 1

HCID 178511263HCID 178511263, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trans-4-(aminomethyl)-cyclohexane carboxylic acid (50 g, 0.318 moles), p-toluenesulfonic acid monhydrate (61.7 g, 0.324 moles), benzyl alcohol (250 mL, 2.4 moles) and 250 mL of toluene were combined and stirred. The mixture was refluxed for 24 hours and the liberated water was removed 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 whereupon the product crystallized. The mixture was vacuum filtered, washed with ether and dried in a vacuum oven to give 128.12 g (96% yield). Greenstein, J. P. and Winitz, M., "Chemistry of the Amino Acids", Robert E. Krieger Publishing Company, Malabar, Fla., Vol. 2, p942 (1986). 1H NMR (CD3OD) 8 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.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customthe liberated water was removed by means of a Dean-Stark apparatus
  3. customA clear solution was obtained after 5 hours
  4. temperatureof refluxing
  5. customcrystallized
  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-297d581a58424b40819563dd7aaef397
Source dataset
uspto-grants-1999_03
Patent number
US05883077

Reaction notes

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