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

HRID 1449964Notes

Reaction equation

HRID 1449964 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. ANALYSIS: Calculated for C12H15ClO4 : 55.71%C 5.84%H Found: 55.61%C 5.92%H

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-eb2fe453873d44bfa021825ad339fe82
Source dataset
uspto-grants-1997_02
Patent number
US05599821

Reaction notes

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