Hydrochloric Acid → 4-Isopropylacetophenone

HRID 2172144Notes

Reaction equation

HRID 2172144 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:14](Cl)(=[O:16])[CH3:15].Cl>C(=S)=S>[CH3:2][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:14]([CH3:15])=[O:16])=[CH:6][CH:5]=1)[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 7406CumeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125784-Isopropylacetophenone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of isopropylbenzene (50 g) in carbon disulfide (250 mL) is treated with aluminum chloride (170 g), and the resulting mixture is cooled to 0° C. Acetyl chloride (33 g) is added at the rate of 1 mL/min, and the resulting mixture is stirred overnight. The mixture is poured into aq. HCl (2N, 400 mL), and the layers are separated. The aqueous phase is extracted with ethyl acetate, and the organic phases are combined, washed with brine, dried over Na2SO4, filtered and concentrated to afford the product, 4-isopropylacetophenone, as an oil (66 g).

Workup

  1. customthe layers are separated
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22958c63ba3442e680271778cf6481e1
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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