Acetic Anhydride → Ethanone, 1-[4-(acetyloxy)-3-[(acetyloxy)methyl]phenyl]-

HRID 905301Notes

Reaction equation

HRID 905301 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[OH:9].[C:13]([O-:16])(=[O:15])[CH3:14].[Na+].[C:18](OC(=O)C)(=[O:20])[CH3:19]>C(O)(=O)C>[C:13]([O:16][CH2:2][C:3]1[CH:4]=[C:5]([C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[O:9][C:18](=[O:20])[CH3:19])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 24048111-[3-(Chloromethyl)-4-hydroxyphenyl]ethan-1-one

Product 1

HCID 154871Ethanone, 1-[4-(acetyloxy)-3-[(acetyloxy)methyl]phenyl]-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

3'-Chloromethyl-4'-hydroxyacetophenone (108 g.) was added to a mixture of anhydrous sodium acetate (54 g.) glacial acetic acid (500 ml.) and acetic anhydride (250 ml.). The mixture was heated at 95° C. for 4 hours, then concentrated by distilling under reduced pressure. The gummy residue was dissolved in water (500 ml.) and the aqueous solution was extracted with chloroform (3×300 ml.). The combined extracts were dried (MgSO4), filtered and evaporated to give a yellow oil. This was distilled under high vacuum to give 3'-acetoxymethyl-4'-acetoxyacetophenone as a colourless viscous liquid (108 g.), b.p. 143°-147° C. (0.3 mm.), which crystallised on cooling to give solid, m.p. 47°-48° C.

Workup

  1. concentrationconcentrated
  2. distillationby distilling under reduced pressure
  3. dissolutionThe gummy residue was dissolved in water (500 ml.)
  4. extractionthe aqueous solution was extracted with chloroform (3×300 ml.)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a yellow oil
  9. distillationThis was distilled under high vacuum

Sources & evidence

ORD record
ord-0312761ab54440afaba556cc06ce23d8
Source dataset
uspto-grants-1983_12
Patent number
US04423070

Reaction notes

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