Potassium Carbonate → HCID 20197276, compound

HRID 652513Notes

Reaction equation

HRID 652513 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][C:17]#[C:18][CH2:19][CH2:20][CH2:21][Cl:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:12]([C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][Cl:22])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 151746641-Bromo-6-chlorohex-2-yne

Product 1

HCID 20197276HCID 20197276, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.10 g of 1-(2,4-dihydroxy-3-propylphenyl) ethanone, 3.13 g of 1-bromo-6-chloro-2-hexyne and 3.30 g of anhydrous potassium carbonate in 35 ml of anhydrous acetone was stirred at reflux for 2.5 hours. The solvent was removed in vacuo, water was added to the residue and the pH was adjusted to 4.0. The product was extracted with ether and the dried (over magnesium sulfate) extract was chromatographed on 250 g of silica gel. Elution with 25% ethyl acetate-hexane gave 4.30 g (88% yield) of 6-(4-acetyl- 3-hydroxy-2-propylphenoxy)-1-chloro-4-hexyne, the titled compound.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe solvent was removed in vacuo, water
  3. additionwas added to the residue
  4. extractionThe product was extracted with ether
  5. dry with materialthe dried (over magnesium sulfate)
  6. extractionextract
  7. customwas chromatographed on 250 g of silica gel
  8. washElution with 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-5f8b2d82af6a49ccbbd73c3d015829df
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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