4'-Hydroxyacetophenone → 1-(4-(Ethoxymethoxy)phenyl)ethanone

HRID 1502220Notes

Reaction equation

HRID 1502220 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][O:19][CH2:20][CH3:21].CO.C(Cl)(Cl)Cl>CC(C)=O>[CH2:20]([O:19][CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH3:21]

Participants

6

Reactant 4

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 21584188Chloroform methanol

Product 1

HCID 571128771-(4-(Ethoxymethoxy)phenyl)ethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 300 milliliter, three-necked oven-dried round bottom flask equipped with a magnetic stirrer, 25 grams (0.18 mole) of 1-(4-hydroxyphenyl)ethanone and 38.6 grams (0.27 mole) of potassium carbonate (K2CO3) were suspended in 200 milliliters of acetone and the mixture was stirred at room temperature for 1 hour, forming a thick slurry. 18.6 grams (0.198 mole) of (chloromethoxy)ethane was slowly added to the reaction mixture using a dropping funnel over a period of one hour and the reaction refluxed overnight for another 12 hours until completion was ascertained by TLC analysis (1:99 methanol/chloroform). The reaction was quenched by pouring the mixture slowly into 400 milliliters of 0.01% hydrochloric acid (HCl) solution, and the product was extracted into 300 milliliters of ethyl acetate, and washed with brine then water to a neutral pH. The ethyl acetate extracts were then dried over sodium sulfate, filtered, and concentrated on a rotary evaporator affording 34.58 grams (˜99% yield) of 1-(4-(ethoxymethoxy)phenyl)ethanone as an oil. The product was used without further purification. 1H NMR (500 MHz, Acetone-d6): δ 7.94-7.91 (d, 2H, 8.5 Hz), 7.13-7.07 (d, 2H, 8 Hz), 5.31 (s, 2H), 3.702-3.67 (q, 2H), 2.49 (s, 3H), 1.16-1.11 (t, 3H).

Workup

  1. customIn a 300 milliliter, three-necked oven-dried round bottom flask equipped with a magnetic stirrer
  2. customforming a thick slurry
  3. customof one hour
  4. temperaturethe reaction refluxed overnight for another 12 hours until completion
  5. customThe reaction was quenched
  6. additionby pouring the mixture slowly into 400 milliliters of 0.01% hydrochloric acid (HCl) solution
  7. extractionthe product was extracted into 300 milliliters of ethyl acetate
  8. washwashed with brine
  9. dry with materialThe ethyl acetate extracts were then dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-71d1e6a8c5df46babfc77ed90f06d24e
Source dataset
uspto-grants-2015_12
Patent number
US09206276B2

Reaction notes

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