2',4'-Dihydroxyacetophenone → 1-(2-Hydroxy-4-octyloxy-phenyl)-ethanone

HRID 18454

Reaction equation

HRID 18454 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=[O:3].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[OH:10][C:9]1[CH:8]=[C:7]([O:11][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:6]=[CH:5][C:4]=1[C:2](=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 69902',4'-DihydroxyacetophenoneHCID 81401-Bromooctane

Product 1

HCID 104680071-(2-Hydroxy-4-octyloxy-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A slurry of 2,4-dihydroxy actophenone (3.8 g; 25 mmol) and KHCO3 (2.75 g; 27.5 mmol) in DMF (50 mL) was stirred at 50° C. for 1 hour and then added 1-bromooctane (4.75 mL; 27.5 mmol). The reaction mixture was stirred at 50-60° C. for 7 days, poured onto H2O (100 mL) and the aqueous phase extracted with diethyl ether (3×). The combined organic fractions was dried (MgSO4), filtered, evaporated to dryness and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10) to yield 4.39 g (66%) as yellow oil. MS (direct; Cl): 265 (MH+).

Workup

  1. additionpoured onto H2O (100 mL)
  2. extractionthe aqueous phase extracted with diethyl ether (3×)
  3. dry with materialThe combined organic fractions was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. custompurified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10)
  7. customto yield 4.39 g (66%) as yellow oil

Sources & evidence

ORD record
ord-608f69a0b7be4c06a95c0fdcf4ccd517
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Linked notes

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