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

HRID 233912Notes

Reaction equation

HRID 233912 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-5546220a44454be38ecd75a99d558012
Source dataset
uspto-grants-1997_01
Patent number
US05593995

Reaction notes

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