Dimethylformamide → HCID 58573710, compound

HRID 2207128Notes

Reaction equation

HRID 2207128 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=O)[CH:12]=[CH:13][CH:14]=1.CN(C)C=O.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(O)C.O>[Cl:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:18])[CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 7964ChlorobenzeneHCID 158793-Chlorophenylacetic acidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58573710HCID 58573710, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

To a mixture of chlorobenzene (170 L, 1684 mol), 3-chlorophenylacetic acid (50 Kg, 293 mol), and dimethylformamide (0.7 L, 9 mol) at 0° C. was added thionyl chloride (39.1 Kg, 329 mol) over the course of 30 min. The mixture was warmed to 15° C. and agitated for 6 h. The mixture was cooled to 0° C. and aluminum chloride (43 Kg, 322 mol) was added over the course of 1.5 h. The mixture was warmed to 20° C. and agitated for 15 h. Water (200 L) and ethanol (200 L) were added to the mixture and the biphasic mixture was agitated for 2 h. The phases were separated and the organic phase was washed twice with aqueous ethylenediaminetetraacetic acid tetrasodium salt (3 wt %, 200 L), and once with water (200 L). Heptane (1600 L) was added to the organic phases over the course of 15 minutes. The suspension was agitated for 30 minutes, cooled to −5° C., and filtered. The filtered material was dried at 40° C. for 20 h. 2-(3-Chlorophenyl)-1-(4-chlorophenyl)ethanone was isolated in 83.6% yield (67.4 Kg).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. temperatureThe mixture was warmed to 20° C.
  3. stirringagitated for 15 h
  4. stirringthe biphasic mixture was agitated for 2 h
  5. customThe phases were separated
  6. washthe organic phase was washed twice with aqueous ethylenediaminetetraacetic acid tetrasodium salt (3 wt %, 200 L)
  7. additionHeptane (1600 L) was added to the organic phases over the course of 15 minutes
  8. stirringThe suspension was agitated for 30 minutes
  9. temperaturecooled to −5° C.
  10. filtrationfiltered
  11. customThe filtered material was dried at 40° C. for 20 h

Sources & evidence

ORD record
ord-d9df0420c49a4db4a72d7dbca97063dc
Source dataset
uspto-grants-2016_06
Patent number
US09376386B2

Reaction notes

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