Benzyl Alcohol → HCID 178511263, compound

HRID 2396443Notes

Reaction equation

HRID 2396443 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

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 and Stark apparatus. A clear solution was obtained after 5 hours of refluxing. The solution was allowed to cool to room temp. 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. 1NMR (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.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customthe liberated water was 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 temp.
  6. customthe product crystallized
  7. filtrationfiltered
  8. washwashed with ether
  9. customdried in a vacuum oven
  10. customto give 128.12 g (96% yield.) Reference

Sources & evidence

ORD record
ord-131e2b7f4c0e4657b6a50a53cc699ba8
Source dataset
uspto-grants-1996_02
Patent number
US05492895

Reaction notes

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