2',4'-Dihydroxyacetophenone → HCID 13477606, compound

HRID 370850Notes

Reaction equation

HRID 370850 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([OH:23])=[CH:20][C:21]=1[OH:22])=[O:15].[N+:24]([C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br)([O-:26])=[O:25]>CC(C)=O.O>[C:14]([C:16]1[CH:17]=[CH:18][C:19]([O:23][CH2:30][C:29]2[CH:28]=[C:27]([N+:24]([O-:26])=[O:25])[CH:34]=[CH:33][CH:32]=2)=[CH:20][C:21]=1[OH:22])(=[O:15])[CH3:13]

Participants

7

Reactant 4

HCID 69902',4'-DihydroxyacetophenoneHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 13477606HCID 13477606, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A mixture of potassium carbonate (anhydrous, 31.7 g) and cesium carbonate (catalytic amount) is pulverized with mortar and pestle, then added to a solution of 2,4-dihydroxyacetophenone (35 g) in acetone (250 ml). The mixture is refluxed for 30 minutes. A solution of m-nitrobenzyl bromide (50 g) in acetone (100 ml) is added in one portion and the reaction refluxed for 3 days. After cooling to room temperature, water is added until a precipitate forms. The product is collected on a Buchner funnel, washed with water and ether. Recrystallization from acetone provides 36.9 g (56% yield) of needles, m.p. 117°-118° C.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. temperaturethe reaction refluxed for 3 days
  3. customThe product is collected on a Buchner funnel
  4. washwashed with water and ether
  5. customRecrystallization from acetone

Sources & evidence

ORD record
ord-2110db5b4daf49999120836915b8dff3
Source dataset
uspto-grants-1985_07
Patent number
US04528392

Reaction notes

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