Reaction #1447086

Reaction equation

D-Homophenylalanine hydrochloride

benzyl alcohol

p-toluenesulfonic acid monohydrate

→

title product

Yield 83.7%

D-Homophenylalanine Benzyl ester Tosylate

Yield 83.7%

Solvents

benzene

Conditions

Workup

1. 1
   Temperatureat reflux in Dean Stark apparatus during 5 hrs
2. 2
   workup.DISTILLATIONafter which time additional benzene (100 mL) was distilled from reaction mixture
3. 3
   OtherThe residue was triturated with diethyl ether
4. 4
   Filtrationthe solid was filtered
5. 5
   Otherdried

Procedure

A solution of D-Homophenylalanine hydrochloride (1.7 g, 7.93 mmol), benzyl alcohol (7.2 mL, 64.0 mmol) and p-toluenesulfonic acid monohydrate (1.8 g, 9.5 mmol) in benzene (30 mL) was heated at reflux in Dean Stark apparatus during 5 hrs, after which time additional benzene (100 mL) was distilled from reaction mixture. The residue was triturated with diethyl ether, the solid was filtered and dried to give title product (2.93 g).

Source