Acetone → 2-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one ethylene ketal

HRID 465436Notes

Reaction equation

HRID 465436 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH2:12]([O:19][C:20]1[C:21](=[O:28])[CH:22]=[C:23]([CH2:26]Cl)[O:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:35][C:36](C)=[O:37]>>[CH2:35]1[O:28][C:21]2([C:20]([O:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:25][O:24][C:23]([CH2:26][O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][C:9]([CH3:10])=[O:11])=[CH:6][CH:7]=3)=[CH:22]2)[O:37][CH2:36]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 37033215-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-oneHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 572178562-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one ethylene ketal

Procedure

A mixture of 4-hydroxyphenylpropan-2-one, ethylene ketal (3.88 g), 5-benzyloxy-2-chloromethyl-4H-pyran-4-one (5.0 g) and potassium carbonate 3.5 g) in acetone, was heated under reflux for 18 h. The reaction mixture was cooled, filtered and the solvent removed in vacuo. The residue was dissolved in ethyl acetate, washed with 2N-sodium hydroxide solution (1×50 ml), water (2×50 ml), dried (magnesium sulphate), filtered and evaporated to dryness in vacuo. The residue was purified by column chromatography on silica using chloroform as eluent, followed by crystallisation from acetone to give 2-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one ethylene ketal, (5.3 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with 2N-sodium hydroxide solution (1×50 ml), water (2×50 ml)
  8. dry with materialdried (magnesium sulphate)
  9. filtrationfiltered
  10. customevaporated to dryness in vacuo
  11. customThe residue was purified by column chromatography on silica
  12. customfollowed by crystallisation from acetone

Sources & evidence

ORD record
ord-4a7eaea6af364feea87a658a778a9858
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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