Benzyl Alcohol → p-Toluenesulfonic acid

HRID 54496

Reaction equation

HRID 54496 reaction equation
C(C(C(C([O-])=O)O)O)([O-])=O.N1CCCC[C@H]1C(O)=O.C(O)C1C=CC=CC=1.O.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>C1C=CC=CC=1.CCOCC>[C:29]1([CH3:39])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 439227Pipecolic acid, (-)-HCID 521998p-Toluenesulfonic acid monohydrateHCID 38061142,3-Dihydroxybutanedioate

Product 1

HCID 6101p-Toluenesulfonic acidYield 185.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a slurry of 7.3 g (26.14 mmol) of the tartrate salt of (S)-pipecolic acid (Egbertson M. and S. J. Danishefsky, J. Org. Chem. 54:11 (1989) in 75 mL of dry benzene was added 13.5 mL (0.13 mol) of benzyl alcohol and 5.48 g (28.8 mmol) of p-toluenesulfonic acid monohydrate. The reaction mixture was heated at reflux under a Dean-Stark trap for 2 h and then cooled to room temperature. The solution was then diluted with 400 mL of ether and stirred overnight at 4° C. The resulting white solid was collected on a filter, washed with hexane and dried in vacuo to give 9.2 g (90%) of the p-toluenesulfonic acid salt of benzyl pipecolate (14). 1H NMR (300 MHz, D2O) δ 7.63 (d), 7.41 (s), 7.28 (d), 5.26 (ABq), 4.8 (s), 4.03 (dd), 3.92 (dd), 3.51-3.39 (m), 3.15-2.93 (s), 2.40 (s), 2.36-2.24 (m), 1.98-1.53 (m).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a Dean-Stark trap for 2 h
  3. customThe resulting white solid was collected on a filter
  4. washwashed with hexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8b1914876ed14971ac26a0132645feb3
Source dataset
uspto-grants-1997_04
Patent number
US05622970

Linked notes

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