Ammonium Chloride → 4-(2'-Chloro-4-biphenylyl)-2-butanone

HRID 1659069Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](Cl)=[O:17])=[CH:10][CH:9]=1.[CH3:19][Mg]Br.[Cl-].[NH4+]>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](=[O:17])[CH3:19])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of β-(2'-chloro-4-biphenylyl)propionyl chloride (28 g.) in anhydrous ether 1 l. is cooled to -70°C. To it is added dropwise a solution of 3M methylmagnesium bromide in ether (34 ml.). The reaction is stirred vigorously throughout. When addition of the grignard is complete (approx. 1 hr), the mixture is allowed to come to room temperature and is decomposed by adding carefully a saturated ammonium chloride solution (approx. 500 ml). The ether phase is washed with brine, dried over sodium sulfate, evaporated in vacuo and the residue distilled to yield 4-(2'-chloro-4-biphenylyl)butan-2-one.

Workup

additionWhen addition of the grignard
custom(approx. 1 hr)
customto come to room temperature
washThe ether phase is washed with brine
dry with materialdried over sodium sulfate
customevaporated in vacuo
distillationthe residue distilled

Sources & evidence

ORD record: ord-32625960888c4a2183b10ddd44fe637f
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03966801

Reaction notes

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