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

HRID 2256607Notes

Reaction equation

HRID 2256607 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-37a8ed1b15064290b1de5e23f74a371b
Source dataset
uspto-grants-1997_08
Patent number
US05654319

Reaction notes

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