Hydrochloric Acid → HCID 10639269, compound

HRID 1780849Notes

Reaction equation

HRID 1780849 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)([CH2:9][OH:10])[CH2:5][CH2:4]1.Cl>CCOCC>[CH:20]1([O:19][C:13]2[CH:12]=[C:11]([C:6]3([CH2:9][OH: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 10594951HCID 10594951, compound

Product 1

HCID 10639269HCID 10639269, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(hydroxymethyl)-cyclohexan-1-one dimethyl ketal (0.15 g, 0.41 mmol) in ether (2 mL) was treated with 1N hydrochloric acid (2 mL) and the mixture was stirred vigorously and gently heated for 10 min. The mixture was extracted with ether, the combined organic extracts were washed with 5% aqueous sodium carbonate, dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 25% ethyl acetate/chloroform, provided a wax (0.06 g, 56%). Analysis Calc. for C19H26O4 : C 71.67, H 8.23; found: C 71.81, H 8.19.

Workup

  1. temperaturegently heated for 10 min
  2. extractionThe mixture was extracted with ether
  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. customPurification by flash chromatography
  7. washeluting with 25% ethyl acetate/chloroform
  8. customprovided a wax (0.06 g, 56%)

Sources & evidence

ORD record
ord-b4753233a8714ee7af4aa2319b624b13
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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