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

HRID 1980392Notes

Reaction equation

HRID 1980392 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[C:10]1([CH:16]([CH3:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>O.ClCCCl>[CH:16]([C:10]1[CH:15]=[CH:14][C:13]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:12][CH:11]=1)([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7406CumeneHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 37734351-(4-isopropylphenyl)propan-1-oneYield 83.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

525 ml of 1,2-dichloroethane and 209 g of aluminium chloride are added to a round flask, which is fitted with a stirrer, thermometer, condenser and dropping funnel. The mixture is cooled to 0° C., and 127 g of propionic acid chloride are allowed to drop in at 0°-5° C. within 3/4 hour. After the addition, the temperature is allowed to rise to +18° C. and then 157 g of cumene are added within 2 hours at 30° C. The mixture is left to stand for 12 hours and the product is then poured into a mixture of 800 g of ice, 130 ml of water and 130 ml of concentrated hydrochloric acid. The aqueous phase is separated and extracted with two 250 ml portions of dichloroethane. The combined organic phases are washed with three 200 ml portions of 2% sodium hydroxide and with 250 ml of water. The solvent is removed by evaporation under a vacuum and the residue (244 g) is distilled over a 10 cm column. There are obtained 192.1 g of p-isopropyl-propiophenone (yield: 83.2% of theory). B.p.=76°-77° C./0.15 mmHg; nD20 =1.5150; d420 =0.9645.

Workup

  1. customwhich is fitted with a stirrer
  2. customthermometer, condenser and dropping
  3. waitto drop in at 0°-5° C. within 3/4 hour
  4. additionAfter the addition
  5. customto rise to +18° C.
  6. waitThe mixture is left
  7. customThe aqueous phase is separated
  8. extractionextracted with two 250 ml portions of dichloroethane
  9. washThe combined organic phases are washed with three 200 ml portions of 2% sodium hydroxide and with 250 ml of water
  10. customThe solvent is removed by evaporation under a vacuum
  11. distillationthe residue (244 g) is distilled over a 10 cm column

Sources & evidence

ORD record
ord-8946cefe5be84272b95daa81762e2b53
Source dataset
uspto-grants-1985_04
Patent number
US04508925

Reaction notes

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