Water → HCID 23051855, compound

HRID 1651379Notes

Reaction equation

HRID 1651379 reaction equation
C([O:3][CH:4]([O:19]CC)[C:5]#[C:6][C:7](=[O:18])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)C.CCOCC.O>O1CCOCC1.Br>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10](/[CH:9]=[CH:8]/[C:7](=[O:18])/[CH:6]=[CH:5]/[C:4]([OH:19])=[O:3])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 23051871HCID 23051871, compound

Product 1

HCID 23051855HCID 23051855, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.0 g (3.47 mmol) of (E)-6,6-diethoxy-1-(p-methoxyphenyl)-1-hexen-4-yn-3-one in 4 ml of dioxane and 2 ml of 2.2N aqueous hydrobromic acid was stirred at 30° for 18 hours and subsequently treated with 20 ml of ether and 10 ml of water. The aqueous phase was extracted twice with ethyl acetate. The combined organic fractions were dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on 80 g of silica gel with acetonitrile/water (1:1). The fractions containing the product were extracted with ethyl acetate. The combined ethyl acetate extracts were dried over magnesium sulphate, filtered and evaporated. The residue was recrystallized from ethyl acetate/hexane, whereby there was obtained (E,E)-6-(p-methoxyphenyl)-4-oxo-2,5-hexadienoic acid of melting point 138°-139°.

Workup

  1. extractionThe aqueous phase was extracted twice with ethyl acetate
  2. dry with materialThe combined organic fractions were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on 80 g of silica gel with acetonitrile/water (1:1)
  6. additionThe fractions containing the product
  7. extractionwere extracted with ethyl acetate
  8. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-20ad31eeee044c318e6d6459e5bc88ea
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

Loading…