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

HRID 2042534Notes

Reaction equation

HRID 2042534 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+].Br[CH2:18][CH2:19][CH2:20][Cl:21]>CC(C)=O>[Cl:21][CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 126856131-[4-(3-Chloropropoxy)phenyl]ethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(4-hydroxyphenyl)ethanone (20.4 g, 150 mmol), K2CO3 (62.1 g, 3.0 eq.), and 3-bromo-1-chloropropane (29.6 mL, 2.0 eq.) in CH3COCH3 (200 mL) was heated to 65° C. overnight. The mixture was filtered, washed with acetone, and concentrated to dryness. The crude product was dissolved in 150 mL of CH2Cl2, and washed with saturated NaHCO3, NaCl solution and dried over Na2SO4. Concentration to dryness under vacuum afforded product (31.5 g, 99% yield): MS m/z 213 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with acetone
  3. concentrationconcentrated to dryness
  4. dissolutionThe crude product was dissolved in 150 mL of CH2Cl2
  5. washwashed with saturated NaHCO3, NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration to dryness under vacuum

Sources & evidence

ORD record
ord-dcfe03a307854f709c3ad35600764b48
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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