Reaction #55883

Reaction equation

3-chloro-4-benzyloxyphenylacetic acid

chloride

thionyl chloride

dimethylaminoethanol

chloride

→

β-dimethylaminoethyl 3-chloro-4-benzyloxyphenylacetate hydrochloride

Yield 131.1%

Solvents

benzene

benzene

Conditions

Workup

1. 1
   Otherso yielding a precipitate which
2. 2
   Filtrationwas filtered
3. 3
   Washwashed with benzene
4. 4
   OtherTwo crystallizations from ethylacetate-isopropyl alcohol (1:1)

Procedure

6.15 grams of 3-chloro-4-benzyloxyphenylacetic acid was converted into the corresponding chloride by treatment with 15 ml of thionyl chloride in 50 ml of benzene. A solution comprising 1.85 grams of dimethylaminoethanol in 10 ml of benzene was slowly added at 20° C. to the chloride solution. The mixture was then permitted to stand for 2 hours at that temperature and then cooled to 5° C., so yielding a precipitate which was filtered and washed with benzene. Two crystallizations from ethylacetate-isopropyl alcohol (1:1) yielded 5.6 grams (68.4%) of β-dimethylaminoethyl 3-chloro-4-benzyloxyphenylacetate hydrochloride, m.p. 138°-140° C.

Source