Benzyl Alcohol → HCID 178427655, compound

HRID 863404Notes

Reaction equation

HRID 863404 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.[NH2:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:10])[CH2:7][CH2:8]1

Participants

5

Reactant 3

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

Product 1

HCID 178427655HCID 178427655, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.0 g (63.6 mmol) of trans-4-aminomethylcyclohexane-1-carboxylic acid, 25.1 g (132 mmol) of 4-toluenesulfonic acid, 50 mL (482 mmol) of benzyl alcohol, and 75 mL of toluene was heated to reflux under a N2 atmosphere using a Dean-Stark trap to collect water formed during the reaction. During reflux, all solids dissolved to leave a colorless solution. After 3 hours at reflux, the solution began to turn yellow. Heat was removed, and the flask allowed to cool to room temperature. The solids which separated out were collected and washed with diethyl ether. There was obtained 24.5 g (58.4 mmol, 92% yield) of product as a white solid. NMR (CD3OD): 7.12/7.20/7.65/7.73 (ABq, C6H4); 7.26 (s, C6H5); 5.06 (s, OCH2 C6H5); 2.72/2.80 (d, CH2N); 2.32 (s, ArCH3); 1.00-2.18 (m, cyclohexyl H). MS: M+ =247 by electron-impact; calculated M+ =247.3.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a N2 atmosphere
  3. customto collect water
  4. customformed during the reaction
  5. temperatureDuring reflux
  6. dissolutionall solids dissolved
  7. customto leave a colorless solution
  8. temperatureAfter 3 hours at reflux
  9. temperatureHeat
  10. customwas removed
  11. customThe solids which separated out
  12. customwere collected
  13. washwashed with diethyl ether

Sources & evidence

ORD record
ord-4b0711b510d14409a214915197b86953
Source dataset
uspto-grants-1998_02
Patent number
US05721214

Reaction notes

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