Hydrochloric Acid → HCID 10594951, compound

HRID 2394503Notes

Reaction equation

HRID 2394503 reaction equation
[CH3:1][O:2][C:3]1([O:25][CH3:26])[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.C1(OC2C=C(C3(CO)CCC(=O)CC3)C=CC=2OC)CCCC1.Cl>CCOCC>[CH3:26][O:25][C:3]1([O:2][CH3:1])[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[CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:12]=2)([CH2:9][OH:10])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131720837HCID 131720837, compound

Product 1

HCID 10594951HCID 10594951, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

15 b. 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one 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 snared 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%).

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-ab508dedf56a48fe9968a03dba147658
Source dataset
uspto-grants-1998_09
Patent number
US05811455

Reaction notes

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