Hydrochloric Acid → HCID 10495633, compound

HRID 1780847Notes

Reaction equation

HRID 1780847 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)([CH:9]=[O:10])[CH2:5][CH2:4]1.Cl>C(OCC)(=O)C>[CH:20]1([O:19][C:13]2[CH:12]=[C:11]([C:6]3([CH:9]=[O:10])[CH2:5][CH2:4][C:3](=[O:2])[CH2:8][CH2:7]3)[CH:16]=[CH:15][C:14]=2[O:17][CH3:18])[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10546597HCID 10546597, compound

Product 1

HCID 10495633HCID 10495633, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-formylcyclohexan-1-one dimethyl ketal (0.1 g, 0.28 mmol) in ethyl acetate (2 mL) was treated with 3N hydrochloric acid (5 mL) and the mixture was stirred vigorously and gently heated for 10 min. The mixture was extracted twice with ethyl acetate, the combined organic extracts were washed with 5% aqueous sodium carbonate, dried (potassium carbonate) and the solvent was removed in vacuo. This material, combined with that obtained from an identical reaction, was purified by flash chromatography, eluting with 2% ethyl acetate/chloroform, to provide a white solid (0.1 g, 57%): m.p. 55°-57° C. Analysis Calc. for C19H24O4 : C 72.13, H 7.65; found: C 72.09, H 7.57.

Workup

  1. temperaturegently heated for 10 min
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washthe combined organic extracts were washed with 5% aqueous sodium carbonate
  4. dry with materialdried (potassium carbonate)
  5. customthe solvent was removed in vacuo
  6. customthat obtained from an identical reaction
  7. customwas purified by flash chromatography
  8. washeluting with 2% ethyl acetate/chloroform

Sources & evidence

ORD record
ord-d93bddf3b8dc4808a9bb5847c6cf5ab4
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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