Potassium Carbonate → HCID 20197276, compound

HRID 1249013Notes

Reaction equation

HRID 1249013 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 anydrous 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-543ff358d0924618afe90407b3a9b7e1
Source dataset
uspto-grants-1986_12
Patent number
US04628115

Reaction notes

Loading…