Water → p-Toluenesulfonic acid

HRID 2082215Notes

Reaction equation

HRID 2082215 reaction equation
N[C@H](C(O)=O)CC1C=CC=CC=1.ClC1C=CC(CO)=CC=1.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.O>C(Cl)(Cl)(Cl)Cl>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6140L-PhenylalanineHCID 133974-Chlorobenzyl alcoholHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of H-Phe-OH (1.65 g), 4-chlorobenzyl alcohol (7.12 g) and p-toluenesulfonic acid monohydrate (2.09 g) in carbon tetrachloride (30 ml) was refluxed for 22 hours while water was removed by molecular sieves 3Al/8. After adding diethyl ether, the white crystal was filtered, washed with diethyl ether and dried to give TsOH.H-Phe-OBzl(Cl) (4.59 g).

Workup

  1. customwas removed by molecular sieves
  2. additionAfter adding diethyl ether
  3. filtrationthe white crystal was filtered
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-4497312aa3c04e54ad086f930975a14e
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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