1,3-Dibromobutane → HCID 14881546, compound

HRID 704376Notes

Reaction equation

HRID 704376 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[CH2:16][CH2:17][CH:18]([Br:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[Br:20][CH:18]([CH3:19])[CH2:17][CH2:16][O:14][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:12])[CH3:13])=[C:9]([OH:10])[C:4]=1[CH2:3][CH2:2][CH3:1]

Participants

6

Reactant 3

HCID 78891,3-DibromobutaneHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 14881546HCID 14881546, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 5.0 g of 2,4-dihydroxy-3-propylacetophenone, 11.1 g of 1,3-dibromobutane, 6.0 g of potassium carbonate and 50 mg of tetra-n-butylammonium bromide in 130 ml of acetone was refluxed overnight. After cooling, the insoluble matter was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1) to give 2.47 g of 1-[4-(3-bromobutoxy)-2-hydroxy-3-propylphenyl]ethanone. Melting point 53°-55° C.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1)

Sources & evidence

ORD record
ord-648a2cfab7c44a46bd9e723313d152dc
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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