Triethylamine → 3-Chloro-propionic acid 2-(4-benzoylphenoxy)ethyl ester

HRID 1183865Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.C(N(CC)CC)C.[Cl:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>CC(=O)CC>[C:9]([C:8]1[CH:17]=[CH:18][C:5]([O:4][CH2:3][CH2:2][O:1][C:29](=[O:30])[CH2:28][CH2:27][Cl:26])=[CH:6][CH:7]=1)(=[O:10])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -10 °C

Procedure

3.6 g (15 mmol) 4-(2-hydroxyethoxy)benzophenone and 1.8 g (18 mmol) triethyl amine were dissolved in 40 ml 2-butanone. The mixture was cooled to −10° C. and 2.3 g (18 mmol) 3-chloro-propionyl chloride was added drop wise while the temperature was kept below −5° C. The reaction was allowed to continue first at 0° C. for 30 minutes, followed by 16 hours at room temperature. The precipitated salts were removed by filtration and the solvent was removed under reduced pressure. The crude 3-chloro-propionic acid 2-(4-benzoylphenoxy)ethyl ester was purified by preparative column chromatography on a Prochrom LC80 column, using n.-hexane/ethyl acetate 70/30 as eluent at a flow rate of 50 ml/min and Kromasil 60A 10 micron as silica. 1.9 g (32%) of 3-chloro-propionic acid 2-(4-benzoylphenoxy)ethyl ester was isolated.

Workup

customwas kept below −5° C
waitfollowed by 16 hours at room temperature
customThe precipitated salts were removed by filtration
customthe solvent was removed under reduced pressure
customThe crude 3-chloro-propionic acid 2-(4-benzoylphenoxy)ethyl ester was purified by preparative column chromatography on a Prochrom LC80 column

Sources & evidence

ORD record: ord-f71accbe4d63406c972b60204b7725eb
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664431B2

Reaction notes

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