Hydrochloric Acid → HCID 10495633, compound

HRID 2394502Notes

Reaction equation

HRID 2394502 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.C1(OC2C=C(C3(C=O)CCC(=O)CC3)C=CC=2OC)CCCC1.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 131720836HCID 131720836, 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 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 mnL) 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.

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-7f4b4de09dee46efab514b3275dddb48
Source dataset
uspto-grants-1998_09
Patent number
US05811455

Reaction notes

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