1,4-Dibromobutane → 4-(4-Acetyl-3-hydroxy-2-propylphenoxy)butyl bromide

HRID 620236Notes

Reaction equation

HRID 620236 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>CCC(C)=O.[I-].[K+]>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:19][CH2:18][CH2:17][CH2:16][Br:15])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 133716024-(4-Acetyl-3-hydroxy-2-propylphenoxy)butyl bromideYield 34.6%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

2', 4'-dihydroxy-3'-(n-propyl)acetophenone (19.1 g), 1,4-dibromobutane (48 ml, 0.4 moles), potassium carbonate (13.8 g), and potassium iodide (50 mg) were combined in MEK (300 ml). The reaction mixture was stirred and heated to reflux temperature overnight then cooled to room temperature. The cooled solution was partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The concentrate was chromatographed on a preparatory-scale HPLC (silica column) eluted with a gradient of 1 to 20% ethyl acetate in hexane to yield 11.2 g of the title product: n.m.r. (300 MHz, CDCl3) δ: 12.8 (s, 1H); 7.6 (d, 1H); 6.45 (d, 1H); 4.1 (t, 2H); 3.55 (t, 2H); 2.7 (t, 2H); 2.65 (s, 3H); 2.25 (m, 2H); 2.05 (m, 2H); 1.58 (m, 2H); 0.98 (t, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux temperature overnight
  3. customThe cooled solution was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe concentrate was chromatographed on a preparatory-scale HPLC (silica column)
  9. washeluted with a gradient of 1 to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-71eadbe877d24c7eac95357c874ca528
Source dataset
uspto-grants-1989_04
Patent number
US04820723

Reaction notes

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