Benzyl Alcohol → p-Toluenesulfonic acid

HRID 466360Notes

Reaction equation

HRID 466360 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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-]S([O-])(=O)=O.[Ca+2]>C(Cl)(Cl)(Cl)Cl.C(OCC)C>[CH2:14]([O:12][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[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

8

Reactant 4

HCID 244Benzyl AlcoholHCID 24497Calcium Sulfate2×HCID 270494-(4-Aminophenyl)butanoic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 2

HCID 6101p-Toluenesulfonic acidHCID 542724484-(4-Aminophenyl)butyric acid benzyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 8.14 g (0.455 mol) of 4-(p-aminophenyl)butyric acid, 34.1 ml of benzyl alcohol and 8.65 g (0.455 mol) of p-toluene sulfonic acid hydrate in 115 ml of carbon tetrachloride is heated overnight at reflux with the solvent return through a tower of Drierite (ca. 30 ml of partially powdered indicating Drierite). The partially cooled mixture is diluted to 600 ml with ethyl ether to give a precipitate which is collected to give 4-(4-aminophenyl)butyric acid benzyl ester, p-toluenesulfonate; m.p. 114°-115° C. This is used in the next reaction without further purification.

Workup

  1. temperatureis heated overnight
  2. customto give a precipitate which
  3. customis collected

Sources & evidence

ORD record
ord-e95fcabc17b447648e9214af064343fe
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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