1,3-Dibromopropane → 1-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone

HRID 986706Notes

Reaction equation

HRID 986706 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].[Br:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:18][CH2:17][CH2:16][Br:15])=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=1[OH:10])(=[O:12])[CH3:13]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,4-dihydroxy-3-propylacetophenone (2.7 g), 1,3-dibromopropane (2.8 ml) and potassium carbonate (1.9 g) in acetone (50 ml) was refluxed for 3 hours. Insoluble materials were filtered off, and the filtrate was concentrated. The resulting syrup was purified by means of a silica gel flash chromatography (chloroform-hexane=1:1) to give 3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl bromide (2.9 g) as colorless and transparent syrup.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationInsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe resulting syrup was purified by means of a silica gel flash chromatography (chloroform-hexane=1:1)

Sources & evidence

ORD record
ord-13760509aab94c0581fae02c6cda87a4
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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