Hydrochloric Acid → 1-(4-iodophenyl)propan-1-one

HRID 532241Notes

Reaction equation

HRID 532241 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:12](Cl)(=[O:15])[CH2:13][CH3:14].Cl>C(=S)=S>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11575IodobenzeneHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2565921-(4-iodophenyl)propan-1-oneYield 38%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
2.5 °C

Procedure

Iodobenzene (100 g, 0.49 mol) was taken in a dry 1 L 3 neck flask equipped with a N2 inlet and to it 200 ml of CS2 was added. The contents were cooled to 0-5° C. and then AlCl3 (80 g, 0.6 moles) and subsequently propionyl chloride (60 g, 0.64 mol) were added while keeping the temperature (internal) at 5-10° C. The contents were stirred for 24 hrs. The reaction mixture was poured into a 5 liter plastic beaker containing 1 L of 10% HCl+1 Kg of crushed ice. The resultant slurry was extracted with 1 L of ethyl acetate. The organic layer was separated and washed with 2×500 ml of water and 500 ml of brine. The organic layer was dried over sodium sulphate and concentrated at 40° C. to give 4′-iodopropiophenone (48 g, 38%).

Workup

  1. additionwas added
  2. customat 5-10° C
  3. additionThe reaction mixture was poured into a 5 liter plastic beaker
  4. extractionThe resultant slurry was extracted with 1 L of ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with 2×500 ml of water and 500 ml of brine
  7. dry with materialThe organic layer was dried over sodium sulphate
  8. concentrationconcentrated at 40° C.

Sources & evidence

ORD record
ord-434dd266653f4dd9a55623d17a2750d7
Source dataset
uspto-grants-2014_10
Patent number
US08853205B2

Reaction notes

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