9-(4-Benzyloxy-phenyl)-bicyclo[3.3.1]nonan-9-ol → 9-(4-Benzyloxy-phenyl)-bicyclo[3.3.1]nonane

HRID 237763Notes

Reaction equation

HRID 237763 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH:20]3[CH2:21][CH2:22][CH2:23][CH:16]2[CH2:17][CH2:18][CH2:19]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH:20]3[CH2:21][CH2:22][CH2:23][CH:16]2[CH2:17][CH2:18][CH2:19]3)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 670610079-(4-Benzyloxy-phenyl)-bicyclo[3.3.1]nonan-9-ol

Product 1

HCID 685293519-(4-Benzyloxy-phenyl)-bicyclo[3.3.1]nonaneYield 123.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

9-(4-Benzyloxy-phenyl)-bicyclo[3.3.1]nonan-9-ol (4.7 g, 14.57 mmol) (prepared in accordance with the procedures set forth in Step 2 of Example 18) was dissolved in EtOH (150 mL) after which concentrated hydrochloric acid (15 mL) was added. This mixture was stirred at 50° C. overnight. The solvent was removed under reduced pressure. Water (50 mL) was added. The mixture was basified with aqueous ammonia and extracted three times with EtOAc. The organic phase was dried and concentrated to provide the title compound (5.5 g).

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. additionWater (50 mL) was added
  4. extractionextracted three times with EtOAc
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-73011340c21b43668ee6c3df638197a1
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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