Hydrochloric Acid → HCID 70529065, compound

HRID 1660068Notes

Reaction equation

HRID 1660068 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C@@H:7]([CH2:10][CH:11]=[CH:12][CH3:13])[C@H:6]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:28])([CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][C:15]=3[O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:5]2)[O:3]C1.Cl>O1CCOCC1>[CH2:30]([O:29][C:15]1[CH:16]=[C:17]([C:20]([CH3:27])([CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:18]=[CH:19][C:14]=1[C@H:6]1[C@H:7]([CH2:10][CH:11]=[CH:12][CH3:13])[CH2:8][CH2:9][C:4](=[O:3])[CH2:5]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86738160HCID 86738160, compound

Product 1

HCID 70529065HCID 70529065, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of trans-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-butenyl)cyclohexanone ethylene ketal (700 mg, 1.38 mmole), dioxane (20 ml) and 2 N hydrochloric acid (20 ml) was heated at reflux for 1.5 hours. The reaction mixture was cooled, poured into ice water (500 ml) and extracted with ether (300 ml). The ether extract was washed with two 200 ml portions of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated to give a quantitative yield of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ether (300 ml)
  5. extractionThe ether extract
  6. washwas washed with two 200 ml portions of saturated sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-9caf9c0fd1344f3fb62edf3a9997b912
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

Loading…