2'-Hydroxyacetophenone → HCID 20560229, compound

HRID 1659315Notes

Reaction equation

HRID 1659315 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH3:11].C(O[C:16](=O)[CH2:17][N:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:19])C>O1CCOCC1>[CH2:20]([N:18]([CH2:17][C:16]1[O:3][C:4]2[C:5]([C:10](=[O:12])[CH:11]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 24758Sodium hydrideHCID 11031023Ethyl 2-[benzyl(methyl)amino]acetate

Product 1

HCID 20560229HCID 20560229, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of sodium hydride (16.4 g) in absolute dioxane (700 ml) stirred at 80° C., was slowly added a mixture of o-hydroxyacetophenone (31.0 g) and N-benzyl-N-methylglycine ethyl ester (40 g) in dioxane (100 ml), and the resulting solution was boiled for 19 hours before being evaporated in vacuo. The residue was dissolved in ethanol and the mixture was saturated with dry HCl and stirred at room temperature for 18 hours. After evaporation the residue was taken up in chloroform and washed with water. Evaporation of the dried organic extracts yielded an oil (40 g) which was chromatographed on alumina eluting with chloroform to give the title chromone as a yellow oil (17.8 g).

Workup

  1. additionwas slowly added
  2. custombefore being evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethanol
  4. stirringstirred at room temperature for 18 hours
  5. customAfter evaporation the residue
  6. washwashed with water
  7. customEvaporation of the dried organic extracts

Sources & evidence

ORD record
ord-4595d5e236714f0b847280a587a8d339
Source dataset
uspto-grants-1981_12
Patent number
US04303656

Reaction notes

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