2-Acetylhydroquinone → 1-(2-Hydroxy-5-propoxyphenyl)ethan-1-one

HRID 1785618Notes

Reaction equation

HRID 1785618 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].C([O-])([O-])=O.[K+].[K+].[CH2:18](I)[CH2:19][CH3:20]>CC(C)=O.CCOC(C)=O.C(Cl)(Cl)Cl>[OH:11][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH2:18][CH2:19][CH3:20])=[CH:9][C:4]=1[C:2](=[O:3])[CH3:1]

Participants

7

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 11430Potassium CarbonateHCID 336431-Iodopropane

Product 1

HCID 155255921-(2-Hydroxy-5-propoxyphenyl)ethan-1-oneYield 89.3%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 g of 2,5-dihydroxyacetophenone suspended in 100 ml of acetone are placed in a 500 ml round-bottomed flask and 9.14 g of anhydrous K2CO3 are added, followed by addition of 12.4 g of propyl iodide. The reaction medium is refluxed for 30 hours. After cooling to room temperature, the medium is filtered through Celite® and then concentrated. The brown oil obtained is taken up in EtOAc, filtered, washed with water, with 2M HCl solution and then with saturated NaCl solution. The organic phase is evaporated to give a black paste. The paste is taken up in chloroform and filtered. The medium is concentrated to give 11.4 g of a black solid. This solid is taken up in absolute ethanol. The solution is placed in a freezer for 10 minutes; a solid precipitates out, and is collected by filtration. The filtrate is concentrated, taken up in ethanol, cooled in a freezer and then filtered again. This operation is repeated four more times to give 8.35 g of the expected compound in the form of a powder.

Workup

  1. customare placed in a 500 ml round-bottomed flask
  2. temperatureThe reaction medium is refluxed for 30 hours
  3. filtrationthe medium is filtered through Celite®
  4. concentrationconcentrated
  5. customThe brown oil obtained
  6. filtrationfiltered
  7. washwashed with water, with 2M HCl solution
  8. customThe organic phase is evaporated
  9. customto give a black paste
  10. filtrationfiltered
  11. concentrationThe medium is concentrated

Sources & evidence

ORD record
ord-eb58f2ccff594f4098f7a85cddd60ef3
Source dataset
uspto-grants-2009_03
Patent number
US07504511B2

Reaction notes

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