Sodium Bicarbonate → 3-[4-(3-Hydroxy-2-oxopropoxymethyl)benzylidene]-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

HRID 251522Notes

Reaction equation

HRID 251522 reaction equation
[OH:1][CH2:2][C:3](OC)([O:25]C)[CH2:4][O:5][CH2:6][C:7]1[CH:24]=[CH:23][C:10]([CH:11]=[C:12]2[C:17]3([CH3:21])[C:18]([CH3:20])([CH3:19])[CH:14]([CH2:15][CH2:16]3)[C:13]2=[O:22])=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+]>O>[OH:1][CH2:2][C:3](=[O:25])[CH2:4][O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH:11]=[C:12]2[C:17]3([CH3:21])[C:18]([CH3:20])([CH3:19])[CH:14]([CH2:15][CH2:16]3)[C:13]2=[O:22])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 672911983-[4-(3-Hydroxy-2,2-dimethoxypropoxymethyl)benzylidene]-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Product 1

HCID 672913013-[4-(3-Hydroxy-2-oxopropoxymethyl)benzylidene]-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-[4-(3-Hydroxy-2,2-dimethoxypropoxymethyl)benzylidene]-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one from Example 8 (2 mmol) is dissolved in the H2O/3N HCl 2:3 mixture (10 ml) and stirred at room temperature for 2 h. A solution of sodium hydrogencarbonate in water is then added dropwise to the reaction mixture with stirring (to about pH=8), and the reaction mixture is extracted with dichloromethane (3×10 ml). The combined organic extracts are dried over magnesium sulfate. The solvent is removed in vacuo, and the residue is purified by column chromatography using (ethyl acetate:cyclohexane—1:1).

Workup

  1. stirringwith stirring (to about pH=8)
  2. extractionthe reaction mixture is extracted with dichloromethane (3×10 ml)
  3. dry with materialThe combined organic extracts are dried over magnesium sulfate
  4. customThe solvent is removed in vacuo
  5. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-dce0935ca14e43b692ac872521357f84
Source dataset
uspto-grants-2011_01
Patent number
US07863478B2

Reaction notes

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