Potassium Carbonate → HCID 12851639, compound

HRID 978136Notes

Reaction equation

HRID 978136 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[CH2:16][CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:16][CH2:17][CH2:18][OH:19])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 12851639HCID 12851639, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.80 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 3.6 ml of 3-bromo-1-propanol and 8.3 g of anhydrous potassium carbonate in 50 ml of anhydrous dimethyl formamide was stirred at 75° for 64 hours. The reaction mixture was concentrated in vacuo, the residue was acidifed and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated in vacuo to 8.7 g of an oil which was chromatographed on 150 g of silica gel. Elution with 40% ethyl acetate-toluene gave 2.84 g which was crystallized from ether-hexane to yield 2.14 g, mp 57°-59°, (28% yield) of 1-[2-hydroxy-4-(3-hydroxypropoxy)-3-propylphenyl]ethanone, the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo to 8.7 g of an oil which
  5. customwas chromatographed on 150 g of silica gel
  6. washElution with 40% ethyl acetate-toluene
  7. customgave 2.84 g which
  8. customwas crystallized from ether-hexane

Sources & evidence

ORD record
ord-245ffc89e151455e8c8dfe9848012135
Source dataset
uspto-grants-1987_05
Patent number
US04663332

Reaction notes

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