Hydrochloric Acid → 1-(4-Hydroxy-3-propyl-phenyl)-propan-1-one

HRID 584282Notes

Reaction equation

HRID 584282 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[CH2:6][CH3:7].[C:15](Cl)(=[O:18])[CH2:16][CH3:17].Cl>[N+](C1C=CC=CC=1)([O-])=O>[OH:14][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:13][C:8]=1[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 125702-PropylphenolHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 223456211-(4-Hydroxy-3-propyl-phenyl)-propan-1-oneYield 35%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
70 °C

Procedure

7.1 g (53 mmol) of aluminum chloride are placed in 70 ml of nitrobenzene in a round-bottomed flask and under a stream of nitrogen. The mixture is heated at 70° C. until dilution is complete. It is then cooled to 0° C. and 7.2 ml (52 mmol) of 2-propylphenol are added. The mixture is allowed to warm to room temperature and is then heated to 40° C. 4.6 ml (52 mmol) of propionyl chloride are then added dropwise. The reaction medium is heated at 40° C. for 2 hours and then stirred for 48 hours at room temperature. It is then poured into ice with 20 ml of concentrated hydrochloric acid. After extraction with ethyl ether, the organic phase is washed with 2N sodium hydroxide. The aqueous phases are acidified with hydrochloric acid and extracted with ether. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The black solid obtained is triturated in heptane, filtered off and dried. 3.5 g (35%) of the expected product are obtained in the form of a black powder.

Workup

  1. temperatureIt is then cooled to 0° C.
  2. temperatureto warm to room temperature
  3. temperatureis then heated to 40° C
  4. temperatureThe reaction medium is heated at 40° C. for 2 hours
  5. extractionAfter extraction with ethyl ether
  6. washthe organic phase is washed with 2N sodium hydroxide
  7. extractionextracted with ether
  8. dry with materialThe organic phase is dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe black solid obtained
  12. customis triturated in heptane
  13. filtrationfiltered off
  14. customdried

Sources & evidence

ORD record
ord-df6452d21af04a61b5a2296380ada0a7
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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