Dimethylformamide → 4'-Benzyloxy-2'-hydroxyacetophenone

HRID 485649Notes

Reaction equation

HRID 485649 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=[O:3].CN(C)C=O.[H-].[Na+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:8][C:9]=1[OH:10])=[O:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 69902',4'-DihydroxyacetophenoneHCID 7503Benzyl ChlorideHCID 24758Sodium hydride

Product 1

HCID 3092574'-Benzyloxy-2'-hydroxyacetophenone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Fifty grams of 2,4-dihydroxyacetophenone were dissolved in 250 ml. of dimethylformamide and the solution was cooled to 0° C. by means of an external ice-bath. After the addition of 15 grams of a 50% oil dispersion of sodium hydride, 40 ml. of benzyl chloride were added in a dropwise fashion and the reaction was allowed to warm to room temperature. After stirring overnight, the reaction mixture was added to 700 ml. of ethyl acetate. The organic phase was washed with 1000 ml. of 1N hydrochloric acid and twice each with 1000 ml. of a saturated sodium chloride solution. The organic layer was dried, and the solvent removed in vacuo. The oily residue was treated with 100 ml. of methanol and 50 ml. of hexane. The desired 2-hydroxy-4-benzyloxyacetophenone (36.7 grams) was recovered by filtration.

Workup

  1. additionthe reaction mixture was added to 700 ml
  2. washThe organic phase was washed with 1000 ml
  3. customThe organic layer was dried
  4. customthe solvent removed in vacuo
  5. additionThe oily residue was treated with 100 ml
  6. filtrationThe desired 2-hydroxy-4-benzyloxyacetophenone (36.7 grams) was recovered by filtration

Sources & evidence

ORD record
ord-d80503ff2fdd4f1cabb56099f49dffa2
Source dataset
uspto-grants-1985_08
Patent number
US04537889

Reaction notes

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