Hydrochloric Acid → 2-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethan-1-one

HRID 2246695Notes

Reaction equation

[Na].C[Si](C)(C)N[Si](C)(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1.[Cl:22][C:23]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:24]=1C(OC)=O.Cl>C1COCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([C:30]2[CH:29]=[CH:24][C:23]([Cl:22])=[CH:32][C:31]=2[Cl:33])=[O:21])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -60 °C

Procedure

420 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to −60° C., under a nitrogen atmosphere, 350 ml of THF are added, and then, dropwise, a solution of 57.6 g of 4-chlorophenylacetic acid in 70 ml of THF and the mixture is kept stirred for 1 hour at −60° C. 66 g of methyl 2,4-dichlorobenzoate are then added, dropwise and at −60° C., the mixture is kept stirred for 40 minutes at −60° C. and then the temperature is allowed to rise to 0° C. The reaction mixture is poured over an ice/1 liter of 2N HCl mixture, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, with water, the organic phase is dried over Na2SO4, the solvent is concentrated under vacuum to a volume of 150 ml, 200 ml of pentane are added and the crystallized product formed is drained. 60 g of the expected compound are obtained.

Workup

customto rise to 0° C
extractionextracted with ether
washthe organic phase is washed with a saturated NaHCO3 solution, with water
dry with materialthe organic phase is dried over Na2SO4
concentrationthe solvent is concentrated under vacuum to a volume of 150 ml, 200 ml of pentane
additionare added
customthe crystallized product formed

Sources & evidence

ORD record: ord-5a4bd523b02945dc8765bc7d54d1f765
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687537B2

Reaction notes

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