Triethylamine → HCID 59609091, compound

HRID 1183863Notes

Reaction equation

[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C(C(C)=O)C>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][C:26](=[O:27])[CH2:25][CH2:24][Cl:23])=[CH:15][CH:14]=1)(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -10 °C

Procedure

6.7 g (35 mmol) of 4-hydroxy-benzophenone was dissolved in 100 ml methyl ethyl ketone. 4.2 g (42 mmol) triethyl amine was added and the mixture was cooled to −10° C. 5.3 g (42 mmol) 3-chloro-propionyl chloride was added drop wise, while the temperature was kept below −5° C. The reaction was allowed to continue for 30 minutes at 0° C. and 3 hours at room temperature. The precipitated salts were removed by filtration and the solvent was evaporated under reduced pressure. 3-Chloro-propionic acid 4-benzoylphenyl ester was isolated by preparative column chromatography on a Prochrom LC80 column, using n-hexane/ethylacetate 75/25 as eluent at a flow rate of 150 ml/min and Kromasil 60A 10 micron as silica. 1.2 g of 3-chloro-propionic acid 4-benzoylphenyl ester was isolated.

Workup

customwas kept below −5° C
customThe precipitated salts were removed by filtration
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-7ac7db95eda0472a88c547ea754a6033
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664431B2

Reaction notes

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