Hydrochloric Acid → 4-Propanoylanisole

HRID 1980394Notes

Reaction equation

HRID 1980394 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[C:10]1([O:16][CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>O.ClCCCl>[CH3:17][O:16][C:10]1[CH:15]=[CH:14][C:13]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 671444-PropanoylanisoleYield 66.4%

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 75 minutes. After the addition, the temperature is allowed to rise to 18° C. and then 141.6 g of anisole are added within 2 hours and at 20° C. The mixture is left to stand for 12 hours and then the product is 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 1,2-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 (198 g) is distilled over a 25 cm column. There are obtained 142 g of p-methoxy-propiophenone (yield: 66.4% of theory). B.p.=90° C./0.4 mmHg; melting point 26° C.; nD20 =1.5451; d420 =0.9645.

Workup

  1. customis fitted with a stirrer
  2. customthermometer, condenser and dropping
  3. additionAfter the addition
  4. customto rise to 18° C.
  5. waitThe mixture is left
  6. waitto stand for 12 hours
  7. customThe aqueous phase is separated
  8. extractionextracted with two 250 ml portions of 1,2-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 (198 g) is distilled over a 25 cm column

Sources & evidence

ORD record
ord-1fc3485bc28a456d9519315df82f075d
Source dataset
uspto-grants-1985_04
Patent number
US04508925

Reaction notes

Loading…