Hydrochloric Acid → Acetophenone hydrochloride

HRID 51517Notes

Reaction equation

HRID 51517 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Br[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)=[O:9].[ClH:23]>CC(O)C>[ClH:23].[O:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[CH2:7][NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:15][CH:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[ClH:23].[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 147976752-Bromo-1-(4-phenoxyphenyl)ethan-1-one

Product 2

HCID 21560873Acetophenone hydrochlorideHCID 22736374HCID 22736374, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Tert-butylamine (15 ml) was added with stirring to a solution of 2-bromo-4′-phenoxyacetophenone (12.7 g, prepared by bromination of 4′-phenoxyacetophenone according to Tetrahedron Letters, 1993, 34, 3177) in propan-2-ol and the mixture heated at 80° C. for 3 hours. The mixture was cooled to 0° C. and concentrated hydrochloric acid (10 ml) added. The suspension was stirred at ambient temperature for 18 hours and the solid collected by filtration to give 4′-phenoxy-2-(tert-butylamino)acetophenone hydrochloride (3.75 g), m.p. 210-212° C. butylamino)acetophenone hydrochloride (3.75 g), m.p. 210-212° C.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-311a6c3b08c242f7adf62979b222fbff
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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