4'-Hydroxyacetophenone → 1-[4-(3-Chloropropoxy)phenyl]ethanone

HRID 2296729Notes

Reaction equation

HRID 2296729 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][Cl:15].[OH-].[K+]>CO>[Cl:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium Hydroxide

Product 1

HCID 126856131-[4-(3-Chloropropoxy)phenyl]ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of p-hydroxyacetophenone (50.7 g, 0.37 mol) and 1-bromo-3-chloropropane (160 ml, 1.5 mol) in methanol (250 mL) was added portionwise potassium hydroxide (63 g, 1.12 mol). The mixture was stirred at reflux for 24 hours, cooled to room temperature, filtered through Celite and evaporated in vacuo. The residual semi-solid was diluted with diethyl ether (500 ml) and washed with H2O (2×300 mL). The ether solution was dried over MgSO4, filtered and evaporated in vacuo to give p-chloropropoxy acetophenone as a liquid in 68% yield (53.38 g). 1H NMR (CDCl3): δ7.98-7.89 (d, J=8.9 Hz, 2H), 7.02-6.92 (d, J=8.9 Hz, 2H), 4.16 (t, J=5.9 Hz, 2H), 3.75 (t, J=6.4 Hz, 2H),2.52 (s, 3H), 2.34-2.16 (m, 2H).

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationfiltered through Celite
  3. customevaporated in vacuo
  4. additionThe residual semi-solid was diluted with diethyl ether (500 ml)
  5. washwashed with H2O (2×300 mL)
  6. dry with materialThe ether solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-25784b64f44e420283a70c3da2ae7642
Source dataset
uspto-grants-2002_12
Patent number
US06489337B1

Reaction notes

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