Hydrochloric Acid → p-t-Butylacetanilide

HRID 1424240Notes

Reaction equation

HRID 1424240 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([NH:11][C:12](=[O:14])[CH3:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:15](Cl)([CH3:18])([CH3:17])[CH3:16].Cl>ClCCCl>[C:15]([C:8]1[CH:9]=[CH:10][C:5]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:7]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 904AcetanilideHCID 10486tert-BUTYL CHLORIDEHCID 6451240Aluminum(III) Chloride

Product 1

HCID 140672p-t-ButylacetanilideYield 86.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A reactor was charged with 1,2-dichloroethane (50 L), followed by aluminum chloride (6.08 kg, 45.6 mol), The mixture was stirred for ten minutes at room temperature and then cooled to 5° C. N-phenylacetamide (5 kg, 37.0 mol) was added slowly, after which the mixture was cooled to −12° C. A solution of t-butylchloride (5.03 kg, 54.3 mol) in 1,2-dichloroethane (5 L) was added to the reaction over ten minutes and then stirred for 1 hour at that temperature. The reaction mixture was added to ice water (50 L) and concentrated hydrochloric acid (2.5 L) at 5-10° C., over one hour. The mixture was heated slowly to 40° C., held at that temperature for thirty minutes and the layers then allowed to separate. The aqueous was extracted further with dichloroethane (50 L) and the combined extracts concentrated, under vacuum, to low volume. Hexane (5 L) was added and the mixture concentrated in vacuo. The residue was slurried with hexane (25 L), cooled to 5° C. and stirred for thirty minutes. The solids were isolated by filtration and dried at room temperature to provide 6.1 kg of the title compound.

Workup

  1. temperaturecooled to 5° C
  2. temperatureafter which the mixture was cooled to −12° C
  3. stirringstirred for 1 hour at that temperature
  4. temperatureThe mixture was heated slowly to 40° C.
  5. waitheld at that temperature for thirty minutes
  6. customto separate
  7. extractionThe aqueous was extracted further with dichloroethane (50 L)
  8. concentrationthe combined extracts concentrated, under vacuum, to low volume
  9. additionHexane (5 L) was added
  10. concentrationthe mixture concentrated in vacuo
  11. temperaturecooled to 5° C.
  12. stirringstirred for thirty minutes
  13. customThe solids were isolated by filtration
  14. customdried at room temperature

Sources & evidence

ORD record
ord-e6da831b648849c6a62a56e0cb888e13
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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