Acetone → 1-[4-(3-Chloropropoxy)-2-hydroxy-5-methoxyphenyl]ethanone

HRID 1082710Notes

Reaction equation

HRID 1082710 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([OH:10])=[CH:8][C:7]([OH:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[Cl:20][CH2:21][CH2:22][CH2:23]Br.CC(C)=O>O>[Cl:20][CH2:21][CH2:22][CH2:23][O:11][C:7]1[C:6]([O:12][CH3:13])=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[C:9]([OH:10])[CH:8]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 498505401-(2,4-Dihydroxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 184672431-[4-(3-Chloropropoxy)-2-hydroxy-5-methoxyphenyl]ethanoneYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,4-dihydroxy-5-methoxyacetophenone (1.4 g, 7.7 mmol), K2CO3 (1.4 g, 10.0 mmol), 3-chlorobromopropane (1.6 g, 10.0 mmol) and acetone (25 mL) was stirred and refluxed under N2 for 16 hours. The reaction was poured into H2O, and the aqueous suspension was extracted with ethyl acetate. The extract was washed (H2O, brine) dried (MgSO4) and concentrated to yield 1.4 g of an off-white solid. Recrystallization twice from ethanol afforded 0.4 g of the alkylated phenol as a solid, m.p. 99°-101 ° C.

Workup

  1. temperaturerefluxed under N2 for 16 hours
  2. extractionthe aqueous suspension was extracted with ethyl acetate
  3. washThe extract was washed (H2O, brine)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9780fb9544924028a6af792d9677e0c6
Source dataset
uspto-grants-1996_12
Patent number
US05589495

Reaction notes

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